Direct preparation of thiazoles, imidazoles, imidazopyridines and

Electronic supporting information

Direct preparation of thiazoles, imidazoles, imidazopyridines and thiazolidines from alkenes

Timothy J. Donohoe,*a Mikhail A Kabeshov,a Akshat Rathi, $a and Ian E. D. Smithb

1H and 13C NMR spectra of the isolated compounds Page 3a 2 3b 4 3c 6 3d 8 3e 10 3f 12 3g 14 3h 16 3i 18 3j 20 3k 22 3l 24 3m 26 3n 28 3o 30 5a 32 5b 34 5c 36 6a 38 6b 40 6c 42 6d 44 6e 46 7a 48 7b 50 7c 52 8a 54 8b 56 9 58

Electronic Supplementary Material (ESI) for Organic & Biomolecular ChemistryThis journal is © The Royal Society of Chemistry 2011

28/02/2010 17:03:43

Formula C10

H10

N2S FW 190.2648

Acquisition Time (sec) 1.9923 Comment W150478 N14038-14-P2 mk772466 1H CDCl3 .. Kabeshov, Mikhail XDate 05 Jan 2010 22:06:56 Date Stamp 05 Jan 2010 22:06:56File Name D:\iodoketones\Suppl_data\N14038-14-P2\N14038-14-P2_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 143.70SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2456.4697Sweep Width (Hz) 8223.18 Temperature (degree C) 20.160

VerticalScaleFactor = 0.5

NS

CH3

NH2

N14038-14-P2_010000fid

8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)

0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

3.041.951.042.032.00

2.39

5.287.29

7.30

7.32

7.38

7.40

7.42

7.55

7.57


28/02/2010 17:16:43

Formula C10

H10

N2S FW 190.2648

Acquisition Time (sec) 1.2517 Comment W150478 N14038-14-P2 mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 05 Jan 2010 23:47:12 Date Stamp 05 Jan 2010 23:47:12File Name D:\iodoketones\Suppl_data\N14038-14-P2\N14038-14-P2_012000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner bruker Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 2896.30SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12023.3662 Sweep Width (Hz) 26177.21Temperature (degree C) 20.160


NS

CH3

NH2

N14038-14-P2_012000fid

184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

12.3

3

76.6

877

.00

77.3

2

117.

41

127.

1312

8.19

128.

30

135.

06

145.

94163.

98


28/02/2010 17:25:52

Formula C11

H13

N3S FW 219.3060

Acquisition Time (sec) 1.9923 Comment W150494 N14038-16-P13 mk772466 1H CDCl3 .. Kabeshov, Mikhail XDate 07 Jan 2010 21:47:44 Date Stamp 07 Jan 2010 21:47:44File Name D:\iodoketones\Suppl_data\N14038-16-P13\N14038-16-P13_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 574.70SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2457.1042 Sweep Width (Hz) 8223.18Temperature (degree C) 21.160


N

NS

NH2

CH3

N14038-16-P13_010000fid

9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)

0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

3.042.072.021.951.000.990.970.96

0.95

0.97

0.99

1.61

1.63

1.65

1.67

1.69

1.70

2.73

2.75

2.76

5.02

7.327.

337.34

7.357.

857.

878.54

8.55

8.78


28/02/2010 17:31:02

Formula C11

H13

N3S FW 219.3060

Acquisition Time (sec) 1.2517 Comment W150494 N14038-16-P13 mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 07 Jan 2010 23:25:52 Date Stamp 07 Jan 2010 23:25:52File Name D:\iodoketones\Suppl_data\N14038-16-P13\N14038-16-P13_012000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner bruker Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 6502.00SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12027.3613 Sweep Width (Hz) 26177.21Temperature (degree C) 21.160


N

NS

NH2

CH3

N14038-16-P13_012000fid

240 220 200 180 160 140 120 100 80 60 40 20 0Chemical Shift (ppm)

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

13.7

3

25.4

029

.00

76.6

877

.00

77.3

2

123.

2512

6.10

131.

3313

5.79

142.

73

148.

2514

9.31

164.

46


28/02/2010 17:39:33

Formula C9H

8N

2S FW 176.2382

Acquisition Time (sec) 1.9923 Comment M68634 N14038-50-P12 mk772466 1H CDCl3 Kabeshov, Mikhail XDate 26 Feb 2010 10:48:32 Date Stamp 26 Feb 2010 10:48:32File Name D:\iodoketones\Suppl_data\N14038-50-P1\N14038-50-P1_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin av400m Original Points Count 16384Owner root Points Count 16384 Pulse Sequence zg30 Receiver Gain 32.00SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2465.5391Sweep Width (Hz) 8223.18 Temperature (degree C) 25.660


NS

NH2

N14038-50-P1_010000fid

8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)

0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

2.030.971.002.012.00

5.24

6.73

7.28

7.30

7.37

7.39

7.41

7.77

7.79


28/02/2010 17:43:51

Formula C9H

8N

2S FW 176.2382

Acquisition Time (sec) 1.2517 Comment W150825 N14038-50-P1 mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 02 Feb 2010 20:35:12 Date Stamp 02 Feb 2010 20:35:12File Name D:\iodoketones\Suppl_data\N14038-50-P1\N14038-50-P1_012000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner bruker Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 14596.50SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12028.1602 Sweep Width (Hz) 26177.21Temperature (degree C) 20.160


NS

NH2

N14038-50-P1_012000fid

192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)

0

0.05

0.10

0.15

0.20

Nor

mal

ized

Inte

nsity

102.

90

125.

9712

8.57

134.

62

151.

33

167.

08


28/02/2010 20:06:52

Formula C13

H18

N4S FW 262.3738

Acquisition Time (sec) 1.9923 Comment W151210 N14038-80-P13 mk772466 1H CDCl3 .. Kabeshov, Mikhail XDate 24 Feb 2010 18:57:04 Date Stamp 24 Feb 2010 18:57:04File Name D:\iodoketones\Suppl_data\N14038-80-P13\N14038-80-P13_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 574.70SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2457.2524 Sweep Width (Hz) 8223.18Temperature (degree C) 21.160


N

N

S

NH2

CH3

NCH3

CH3

N14038-80-P13_010000fid

10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)

0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

3.172.082.096.151.951.051.001.00

0.94

0.96

0.98

1.591.

611.62

1.64

1.66

1.68

2.702.

722.

74

3.12

4.966.

556.

57

7.27

7.66

7.67

7.698.

308.

31


28/02/2010 20:09:54

Formula C13

H18

N4S FW 262.3738



N

N

S

NH2

CH3

NCH3

CH3

N14038-80-P13_012000fid


0

0.05

0.10

0.15

0.20

0.25

Nor

mal

ized

Inte

nsity

13.8

0

25.4

529

.13

38.1

9

105.

42

119.

3012

3.10

137.

51

147.

22

158.

24

164.

01


28/02/2010 18:12:06

Formula C9H

11N

3S

2FW 225.3337



NS

NS

CH3

NH2

N14038-64-P12_010000fid

10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)

0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

3.102.102.082.051.000.98

0.99

1.01

1.03

1.63

1.65

1.66

1.68

1.70

1.72

2.77

2.79

2.81

5.37

8.01

8.73


28/02/2010 18:17:09

Formula C9H

11N

3S

2FW 225.3337



NS

NS

CH3

NH2

N14038-64-P12_012000fid

192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8Chemical Shift (ppm)

0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

13.7

5

24.5

029.0

7

125.

45

133.

3213

6.35

140.

14

151.

76

164.

52


28/02/2010 19:59:57

Formula C11

H12

N2OS FW 220.2908



N S

NH2

OCH3

N14038-78-P12_010000fid


0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

3.022.031.991.011.972.003.

39

4.49

5.31

7.33

7.35

7.377.

407.

427.

447.

577.

59


28/02/2010 19:59:13

Formula C11

H12

N2OS FW 220.2908



N S

NH2

OCH3

N14038-78-P12_012000fid


0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

57.7

3

66.4

4

118.

97

127.

9012

8.34

128.

51

134.

51

149.

64166.

15


0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

-500

0

500

1000

1500

2000

2500

3000

3500

4000

4500

5000

5500

6000

3.08

0.99

1.01

0.98

1.01

1.00

0.00

2.67

3.34

3.35

3.35

3.35

3.36

4.70

6.84

7.48

7.50

7.52

7.88

7.90

7.95

8.35

8.35

8.36

S

N

NH2

CH3O

Parameter Value

1 Solvent MeOD

2 Pulse Sequence zg30

3 Acquisition Date 2010-11-18T21:55:59

4 Number of Scans 16

5 Spectrometer Frequency 400.13

6 Spectral Width 8278.1

7 Lowest Frequency -1660.1

8 Nucleus 1H

9 Acquired Size 32768

10 Spectral Size 65536


0102030405060708090100110120130140150160170180190200210220230240250f1 (ppm)

0

2000

4000

6000

8000

10000

12000

14000

16000

18000

20000

22000

24000

26000

28000

30000

32000

3400027.0

3

48.5

148

.72

48.9

449

.15

49.3

649

.58

49.7

9

77.9

878

.31

78.6

3

103.

77

126.

6012

8.07

129.

6313

1.34

136.

0013

7.97

150.

11

170.

58

200.

24S

N

NH2

CH3O

Parameter Value

1 Solvent MeOD

2 Pulse Sequence zgpg30






8 Nucleus 13C




-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)

0

500

1000

1500

2000

2500

3000

1.95

1.98

1.98

1.00

2.49

2.50

2.50

2.50

2.51

3.32

7.10

7.23

7.24

7.25

7.26

7.27

7.78

7.80

7.81

8.52

8.53

S

N

NH2

N

Parameter Value

1 Solvent DMSO







8 Nucleus 1H




-100102030405060708090100110120130140150160170180190200210220230240250f1 (ppm)

-10000

0

10000

20000

30000

40000

50000

60000

70000

80000

90000

1E+05

1E+05

1E+05

1E+05

47.3

547

.56

47.7

847

.99

48.2

048

.42

48.6

3

106.

29

121.

2512

2.73

137.

76

148.

9414

9.92

152.

80

170.

24

N

SN

NH2

Parameter Value

1 Solvent MeOD

2 Pulse Sequence zgdc30






8 Nucleus 13C




0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)

0

1000

2000

3000

4000

5000

6000

7000

8000

9000

10000

3.25

2.17

2.13

1.02

1.08

2.07

1.00

-0.0

0

1.40

1.41

1.43

4.38

4.39

4.41

4.43

5.20

6.82

7.43

7.45

7.47

7.95

7.96

7.96

7.98

8.42

8.42

8.43

SN

NH2

OO

CH3

Parameter Value

1 Solvent CDCl3







8 Nucleus 1H




-100102030405060708090100110120130140150160170180190200210220230240f1 (ppm)

-5000

0

5000

10000

15000

20000

25000

30000

35000

40000

45000

50000

55000

60000

65000

14.3

7

61.0

5

76.6

877

.00

77.3

2

103.

70

126.

9912

8.64

128.

6713

0.28

130.

8513

4.91

150.

33

166.

5516

7.37

SN

NH2

OO

CH3

Parameter Value

1 Solvent CDCl3







8 Nucleus 13C




0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)

0

500

1000

1500

2000

2500

3000

3500

4000

4500

5000

2.94

1.93

1.03

4.00

2.49

2.50

2.50

2.50

2.51

3.34

3.85

7.16

7.25

7.91

7.92

7.92

7.94

7.94

7.96

7.96

7.97

SN

NH2

O

OCH3

Parameter Value

1 Solvent DMSO







8 Nucleus 1H




0102030405060708090100110120130140150160170180190200210f1 (ppm)

-1000

0

1000

2000

3000

4000

5000

6000

7000

8000

9000

10000

11000

12000

28.3

728

.56

28.7

528

.95

29.1

429

.33

29.5

2

51.3

4

104.

29

125.

6512

8.61

129.

54

139.

45

149.

67

166.

1416

8.24

205.

0520

5.26

205.

45

SN

NH2

O

OCH3

Parameter Value

1 Solvent Acetone







8 Nucleus 13C




0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)

-1000

0

1000

2000

3000

4000

5000

6000

7000

8000

9000

10000

11000

12000

13000

14000

15000

16000

17000

18000

19000

20000

21000

3.11

2.00

0.93

3.10

0.98

0.00

2.39

2.44

5.18

6.45

7.18

7.19

7.20

7.21

7.22

7.51

7.51

7.52

7.53

SN

NH2

CH3Parameter Value

1 Solvent CDCl3







8 Nucleus 1H




-100102030405060708090100110120130140150160170180190200210220230240f1 (ppm)

-2000

0

2000

4000

6000

8000

10000

12000

14000

16000

18000

20000

22000

24000

26000

28000

30000

32000

34000

21.0

2

76.6

877

.00

77.3

2

105.

67

125.

7012

7.75

129.

5313

0.66

134.

8813

5.99

151.

32

166.

43

SN

NH2

CH3

Parameter Value

1 Solvent CDCl3







8 Nucleus 13C




-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

-500

0

500

1000

1500

2000

2500

3000

3500

4000

4500

5000

5500

6000

3.02

1.03

2.00

1.85

2.00

2.49

2.50

2.50

2.50

2.51

3.34

3.76

6.82

6.90

6.93

7.01

7.70

7.71

7.72

7.73

O

SN

NH2

CH3

Parameter Value

1 Solvent DMSO







8 Nucleus 1H




0102030405060708090100110120130140150160170180190200210f1 (ppm)

-1000

0

1000

2000

3000

4000

5000

6000

7000

8000

9000

10000

1100038.8

839

.09

39.3

039

.51

39.7

239

.93

40.1

4

55.0

7

99.3

0

113.

79

126.

8012

7.84

149.

66

158.

49

168.

04

O

SN

NH2

CH3

Parameter Value

1 Solvent DMSO







8 Nucleus 13C




0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)

-50

0

50

100

150

200

250

300

350

400

450

500

550

600

650

700

750

800

850

2.01

2.07

2.01

3.24

1.00

-0.0

0

2.83

2.83

2.85

2.86

2.87

3.01

3.03

3.05

5.01

7.12

7.13

7.14

7.15

7.16

7.16

7.17

7.18

7.22

7.26

7.67

7.69

S

N

NH2

Parameter Value

1 Solvent CDCl3







8 Nucleus 1H




0102030405060708090100110120130140150160170180190200f1 (ppm)

0

5000

10000

15000

20000

25000

30000

35000

40000

45000

21.0

7

28.4

7

38.8

839

.09

39.3

039

.51

39.7

239

.93

40.1

4

117.

52

122.

11

126.

18

131.

6613

4.23

144.

28

166.

56S

N

NH2Parameter Value

1 Solvent DMSO







8 Nucleus 13C




23/03/2010 22:38:00

Formula C11

H20

N2S FW 212.3549

Acquisition Time (sec) 1.9923 Comment W151489 N14038-91-P12 mk772466 1H CDCl3 .. Kabeshov, Mikhail XDate 11 Mar 2010 22:06:56 Date Stamp 11 Mar 2010 22:06:56File Name G:\iodoketones\Suppl_data\N14038-91-P12\N14038-91-P12_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 90.50SW(cyclical) (Hz) 8223.68 Solvent CHLOROFORM-d Spectrum Offset (Hz) 2457.2363 Sweep Width (Hz) 8223.18Temperature (degree C) 20.160


S

N

CH3

CH3

NH2

N14038-91-P12_010000fid

9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)

0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

5.934.003.992.012.001.96

0.90

0.92

0.93

1.29

1.31

1.33

1.34

1.36

1.47

1.54

1.56

1.58

1.59

2.40

2.42

2.56

2.57

4.90


23/03/2010 22:42:02

Formula C11

H20

N2S FW 212.3549

Acquisition Time (sec) 1.2517 Comment W151489 N14038-91-P12 mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 11 Mar 2010 23:45:04 Date Stamp 11 Mar 2010 23:45:04File Name G:\iodoketones\Suppl_data\N14038-91-P12\N14038-91-P12_012000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner bruker Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 5792.60SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12026.5625 Sweep Width (Hz) 26177.21Temperature (degree C) 20.160


S

N

CH3

CH3

NH2

N14038-91-P12_012000fid

192 184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8 0Chemical Shift (ppm)

0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

13.8

313

.95

22.1

222

.52

28.7

331

.8234

.10

121.

88

147.

08

164.

03


0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

-100

0

100

200

300

400

500

600

700

800

900

1000

1100

1200

1300

1400

6.04

2.99

1.00

1.98

-0.0

0

1.19

1.21

2.13

3.04

3.05

3.07

3.09

3.10

7.26

CH3

SN

NH2

CH3CH3

Parameter Value

1 Solvent CDCl3







8 Nucleus 1H




-100102030405060708090100110120130140150160170180190200210220230240250f1 (ppm)

-2000

-1000

0

1000

2000

3000

4000

5000

6000

7000

8000

9000

10000

11000

12000

13000

14000

15000

16000

17000

18000

19000

20000

21000

14.6

2

24.8

527

.08

76.6

877

.00

77.3

2

129.

63

140.

30

163.

70

CH3

SN

NH2

CH3CH3

Parameter Value

1 Solvent CDCl3







8 Nucleus 13C




0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.011.512.0f1 (ppm)

-500

0

500

1000

1500

2000

2500

3000

3500

4000

4500

5000

5500

6000

6500

7000

7500

1.01

1.02

1.00

4.38

2.04

0.96

0.90

-0.0

0

6.41

6.43

6.72

6.98

7.18

7.27

7.29

7.81

7.83

7.83

8.25

8.26

10.1

5

SN

NH

N

Parameter Value

1 Solvent CDCl3







8 Nucleus 1H




0102030405060708090100110120130140150160170180190200210f1 (ppm)

-2000

-1000

0

1000

2000

3000

4000

5000

6000

7000

8000

9000

10000

11000

12000

13000

14000

15000

16000

17000

18000

19000

20000

21000

76.6

877

.00

77.3

2

105.

67

110.

58

116.

22

126.

1312

7.75

128.

70

134.

7213

7.44

146.

6214

9.31

151.

33

161.

07

SN

NH

N

Parameter Value

1 Solvent CDCl3







8 Nucleus 13C




28/02/2010 20:18:43

Formula C14

H10

N2S FW 238.3076



N

S

N

N14038-81-P12_010000fid

10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)

0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

4.251.022.081.001.000.97

7.37

7.38

7.41

7.45

7.47

7.55

8.00

8.02

8.33

8.358.

688.

68

9.26

9.26


28/02/2010 20:21:49

Formula C14

H10

N2S FW 238.3076



N

S

N

N14038-81-P12_012000fid

184 176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16Chemical Shift (ppm)

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

113.

23

123.

6812

6.41

128.

7812

9.67

133.

6213

4.03

147.

7215

0.77

156.

70

164.

30


28/02/2010 18:36:31

Formula C13

H15

NS FW 217.3299



N S

CH3CH3

CH3

N14038-65-P12_010000fid

11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)

0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

9.301.982.022.00

1.51

7.307.

327.

347.

437.

457.93

7.95


28/02/2010 18:39:37

Formula C13

H15

NS FW 217.3299



N S

CH3CH3

CH3

N14038-65-P12_012000fid

230 220 210 200 190 180 170 160 150 140 130 120 110 100 90 80 70 60 50 40 30Chemical Shift (ppm)

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

30.9

2

37.7

9

111.

35

126.

3312

8.61

134.

92

154.

57

180.

88


28/02/2010 18:54:13

Formula C12

H14

N2

FW 186.2530



N NH

CH3

N14038-68-P12_010000fid

9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)

0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

3.032.012.041.981.992.00

0.93

0.95

0.97

1.70

1.72

1.74

1.76

1.77

1.79

2.70

2.72

2.74

7.21

7.23

7.36

7.37

7.68

7.70


25/04/2010 12:36:57

Formula C12

H14

N2

FW 186.2530

Acquisition Time (sec) 1.0420 Comment DPX250 13C Acquisition Date 24 Apr 2010 08:19:12Date Stamp 24 Apr 2010 08:19:12 File Name G:\MK-GSK-250\MK-GSK-250_003000fidFrequency (MHz) 62.90 Nucleus 13C Number of Transients 30000 Origin dpx250Original Points Count 16384 Owner root Points Count 16384 Pulse Sequence zgpg30Receiver Gain 512.00 SW(cyclical) (Hz) 15723.27 Solvent CHLOROFORM-dSpectrum Offset (Hz) 6888.0454 Sweep Width (Hz) 15722.31 Temperature (degree C) 26.023


N NH

CH3

MK-GSK-250_003000fid


0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

Nor

mal

ized

Inte

nsity

13.7

3

22.0

2

30.3

0

115.

13

124.

7512

6.78

128.

6713

2.56

137.

36

149.

39


28/02/2010 17:57:26

Formula C14

H11

N3

FW 221.2572

Acquisition Time (sec) 1.9923 Comment W151170 N14038-61-P13 mk772466 1H MeOD .. Kabeshov, Mikhail XDate 23 Feb 2010 22:43:12 Date Stamp 23 Feb 2010 22:43:12File Name D:\iodoketones\Suppl_data\N14038-61-P14\N14038-61-P14_010000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 16 Origin dpx400n Original Points Count 16384Owner chemist Points Count 16384 Pulse Sequence zg30 Receiver Gain 287.40SW(cyclical) (Hz) 8223.68 Solvent MeOD Spectrum Offset (Hz) 2463.0754 Sweep Width (Hz) 8223.18Temperature (degree C) 20.160


NNH

N

N14038-61-P14_010000fid

11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0Chemical Shift (ppm)

0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

1.012.051.991.991.001.000.92

7.25

7.27

7.38

7.40

7.54

7.77

7.78

8.34

8.36

8.538.54

9.12


25/04/2010 12:19:37

Formula C14

H11

N3

FW 221.2572

Acquisition Time (sec) 1.1796 Comment DRX500 13C acquisition BBO probe Date 25 Apr 2010 08:36:16Date Stamp 25 Apr 2010 08:36:16 File Name G:\MK-GSK-500\MK-GSK-500_004000fidFrequency (MHz) 125.77 Nucleus 13C Number of Transients 25000 Origin drx500Original Points Count 32768 Owner root Points Count 32768 Pulse Sequence zgpg30Receiver Gain 32768.00 SW(cyclical) (Hz) 27777.78 Solvent CHLOROFORM-dSpectrum Offset (Hz) 12515.2432 Sweep Width (Hz) 27776.93 Temperature (degree C) 24.996


N NH

N



0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

118.

42

124.

1712

5.04

126.

6112

7.38

128.

75

131.

76

134.

05

139.

36

143.

6714

5.61

148.

44


28/02/2010 19:40:56

Formula C11

H12

N2S FW 204.2914



NH N

S

CH3

N14038-77-P12_010000fid

10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)

0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

Nor

mal

ized

Inte

nsity

3.042.011.403.032.00

1.29

1.31

1.33

3.02

3.03

3.05

3.07

7.24

7.25

7.27

7.36

7.37

7.39

7.69

7.71


25/04/2010 14:18:11

Formula C11

H12

N2S FW 204.2914

Acquisition Time (sec) 1.2517 Comment W152180 N14038-IM-1A mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 21 Apr 2010 20:03:12 Date Stamp 21 Apr 2010 20:03:12File Name G:\iodoketones\Suppl_data\N14038-77-P12\W152180_11\W152180_11_011000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner chemist Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 9195.20SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12027.3613 Sweep Width (Hz) 26177.21Temperature (degree C) 22.160


N NH

S

CH3

W152180_11_011000fid

176 168 160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8Chemical Shift (ppm)

0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

Nor

mal

ized

Inte

nsity

15.2

6

29.4

5

117.

61

124.

7612

7.10

128.

71

132.

25

139.

9314

0.63


28/02/2010 19:12:07

Formula C13

H14

N2

FW 198.2637



N N

N14038-69-P12_010000fid

9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)

0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

4.222.052.081.000.982.012.00

1.95

1.97

1.98

1.99

2.00

2.92

2.94

2.953.96

3.98

3.99

7.07

7.19

7.21

7.33

7.35

7.37

7.74

7.75


28/02/2010 19:15:17

Formula C13

H14

N2

FW 198.2637



N N

N14038-69-P12_012000fid

160 152 144 136 128 120 112 104 96 88 80 72 64 56 48 40 32 24 16 8Chemical Shift (ppm)

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

21.1

323.0

124

.60

44.8

1

113.

80

124.

6012

6.37

128.

42

134.

40

140.

47

145.

18


23/03/2010 22:26:44

Formula C17

H16

N2O FW 264.3217



N

NH

OCH3

N14038-90-P12_010000fid


0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

3.052.016.182.001.993.

41

4.57

7.27

7.317.

337.367.

387.41

7.60

7.61

7.86

7.88


25/04/2010 12:30:26

Formula C17

H16

N2O FW 264.3217

Acquisition Time (sec) 1.1796 Comment DRX500 13C acquisition BBO probe Date 24 Apr 2010 08:19:12Date Stamp 24 Apr 2010 08:19:12 File Name G:\MK-GSK-500\MK-GSK-500_002000fidFrequency (MHz) 125.77 Nucleus 13C Number of Transients 30000 Origin drx500Original Points Count 32768 Owner root Points Count 32768 Pulse Sequence zgpg30Receiver Gain 6502.00 SW(cyclical) (Hz) 27777.78 Solvent CHLOROFORM-dSpectrum Offset (Hz) 12513.5479 Sweep Width (Hz) 27776.93 Temperature (degree C) 24.996


N NH

OCH3


160 155 150 145 140 135 130 125 120 115 110 105 100 95 90 85 80 75 70 65 60 55 50Chemical Shift (ppm)

0.05

0.10

0.15

0.20

0.25

Nor

mal

ized

Inte

nsity

58.0

0

66.0

0

125.

5012

7.34

128.

6012

8.73

128.

8212

9.45

131.

74

135.

46

145.

94


0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.0f1 (ppm)

-1000

0

1000

2000

3000

4000

5000

6000

7000

8000

9000

10000

11000

12000

13000

14000

0.99

1.00

1.01

2.03

0.99

1.00

1.99

1.02

6.77

6.78

6.80

7.16

7.18

7.44

7.64

7.86

7.95

7.97

7.97

8.11

8.13

NN

Parameter Value

1 Solvent CDCl3







8 Nucleus 1H




0102030405060708090100110120130140150160170180190200f1 (ppm)

0

20

40

60

80

100

120

140

160

180

200

220

240

260

280

300

320

340

360

380

76.6

877

.00

77.3

2

108.

09

112.

57

117.

44

124.

87

128.

7213

3.43

145.

51

NN

Parameter Value

1 Solvent CDCl3







8 Nucleus 13C




0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.511.011.512.012.5f1 (ppm)

0

500

1000

1500

2000

2500

3000

3500

4000

1.00

1.01

1.04

2.07

3.05

1.03

3.30

3.31

3.31

3.31

3.32

6.43

6.43

6.45

6.45

6.53

6.53

7.25

7.27

7.29

7.40

7.79

8.02

8.02

8.04

8.04

NN

NH2

Parameter Value

1 Solvent MeOD







8 Nucleus 1H




0102030405060708090100110120130140150160170180190200210f1 (ppm)

-5000

0

5000

10000

15000

20000

25000

30000

35000

40000

45000

50000

55000

60000

65000

70000

48.5

148

.72

48.9

449

.15

49.3

649

.58

49.7

9

93.6

6

108.

0910

8.35

126.

8012

7.91

128.

6512

9.76

135.

35

144.

97

149.

2314

9.90

NN

NH2

Parameter Value

1 Solvent MeOD







8 Nucleus 13C




0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)

0

500

1000

1500

2000

2500

3000

3500

4000

1.02

1.02

2.01

1.05

1.00

1.99

0.96

0.00

7.22

7.23

7.25

7.25

7.26

7.33

7.35

7.36

7.37

7.37

7.37

7.43

7.45

7.46

7.47

7.52

7.55

7.84

7.95

8.28

8.28

8.28

8.28

NN Br

Parameter Value

1 Solvent CDCl3







8 Nucleus 1H




0102030405060708090100110120130140150160170180190200f1 (ppm)

-500

0

500

1000

1500

2000

2500

3000

3500

4000

4500

5000

5500

6000

6500

7000

7500

8000

76.6

877

.00

77.3

2

106.

9710

8.25

118.

14

125.

5412

6.07

128.

7913

3.20

144.

1014

6.67

NN Br

Parameter Value

1 Solvent CDCl3







8 Nucleus 13C




-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

0

500

1000

1500

2000

2500

3000

3500

4000

4500

5000

6.16

3.19

3.18

3.13

1.03

1.03

1.00

4.82

-0.0

0

1.18

1.19

1.24

1.27

1.28

1.45

1.47

1.58

2.28

3.04

3.06

3.07

3.72

3.73

3.75

5.50

7.20

7.20

7.21

7.24

7.26

7.30

7.31

7.32

7.33

7.34

SN

N

CH3

CH3

CH3

CH3

CH3

Parameter Value

1 Solvent CDCl3







8 Nucleus 1H




-100102030405060708090100110120130140150160170180190200210220230240250f1 (ppm)

-500

0

500

1000

1500

2000

2500

3000

3500

4000

4500

5000

5500

6000

6500

18.6

819

.51

19.8

123

.46

23.5

3

49.7

1

56.5

8

76.6

877

.00

77.3

2

93.4

8

125.

6212

8.99

130.

46

138.

1013

9.51

154.

19

SN

N

CH3

CH3

CH3

CH3

CH3

Parameter Value

1 Solvent CDCl3







8 Nucleus 13C




0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)

-200

0

200

400

600

800

1000

1200

1400

1600

1800

2000

2200

2400

2600

2800

3000

3200

3400

3600

3800

3.02

3.03

0.92

4.00

4.31

-0.0

0

2.27

3.13

5.71

7.00

7.01

7.03

7.05

7.06

7.06

7.22

7.24

7.24

7.26

7.27

7.29

7.31

7.35

7.35

7.37

7.38

Parameter Value

1 Solvent CDCl3







8 Nucleus 1H



SN

N

F

CH3

CH3


0102030405060708090100110120130140150160170180190200f1 (ppm)

-2000

-1000

0

1000

2000

3000

4000

5000

6000

7000

8000

9000

10000

11000

12000

13000

14000

15000

16000

17000

18000

19000

20000

21000

22000

23000

19.5

9

32.0

9

76.6

877

.00

77.3

2

94.6

3

115.

8811

6.10

122.

7112

2.79

126.

08

129.

6413

0.42

137.

8413

9.31

147.

87

157.

6816

0.07

160.

33S

N

N

F

CH3

CH3

Parameter Value

1 Solvent CDCl3







8 Nucleus 13C




23/03/2010 22:11:42

Formula C16

H15

NO2

FW 253.2958



NH

O

CH3

OCH3

N14038-88-P12_010000fid

11.5 11.0 10.5 10.0 9.5 9.0 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5Chemical Shift (ppm)

0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

0.45

0.50

Nor

mal

ized

Inte

nsity

3.283.231.011.031.001.982.092.141.003.

873.

95

6.25

6.53

6.87

7.27

7.42

7.44

7.60

7.62

8.26


23/03/2010 22:18:24

Formula C16

H15

NO2

FW 253.2958

Acquisition Time (sec) 1.2517 Comment W151421 N14038-88-P12 mk772466 13C CDCl3 .. Kabeshov, Mikhail XDate 09 Mar 2010 22:00:32 Date Stamp 09 Mar 2010 22:00:32File Name G:\iodoketones\Suppl_data\N14038-88-P12\N14038-88-P12_012000fid Frequency (MHz) 100.62Nucleus 13C Number of Transients 2048 Origin dpx400n Original Points Count 32768Owner bruker Points Count 32768 Pulse Sequence zgdc30 Receiver Gain 9195.20SW(cyclical) (Hz) 26178.01 Solvent CHLOROFORM-d Spectrum Offset (Hz) 12027.3623 Sweep Width (Hz) 26177.21Temperature (degree C) 20.160


NH

O

CH3

OCH3

N14038-88-P12_012000fid


0

0.05

0.10

0.15

0.20

0.25

0.30

0.35

0.40

Nor

mal

ized

Inte

nsity

55.3

755

.67

86.7

2

91.9

2

97.1

3

114.

47

124.

4412

6.96

128.

95

132.

5113

5.06

138.

05

153.

67

157.

83


Direct preparation of thiazoles, imidazoles, imidazopyridines and

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Transcript of Direct preparation of thiazoles, imidazoles, imidazopyridines and