Supporting information · Sonu Kumar, Rakesh K. Saunthwal, Trapti Aggarwal, Siva K. Reddy Kotla and...
Transcript of Supporting information · Sonu Kumar, Rakesh K. Saunthwal, Trapti Aggarwal, Siva K. Reddy Kotla and...
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Supporting Information Palladium Meets Copper: One-Pot Tandem Synthesis of
Pyrido Fused Heterocycle via Sonogashira conjoined
Electrophilic Cyclization
Sonu Kumar, Rakesh K. Saunthwal, Trapti Aggarwal, Siva K. Reddy Kotla and Akhilesh K.
Verma*
Synthetic Organic Chemistry Research Laboratory, Department of Chemistry,
University of Delhi, Delhi – 110007, India
Email: [email protected]
S. No. Table of contents Page No.
1 X-ray crystallographic studies 2-3
2 References 4-4
3 Copies of 1H NMR, 13C NMR and HRMS 5-104
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2016
2
X-ray crystallographic studies
.
Figure 1. ORTEP drawing of compound 4b drawn at 50% probability level .
The crystal of compound 4b (CCDC No: 1486060) was generated in CH2Cl2/Hexane. The
intensity data for SON-387 was collected on an Bruker Kappa Apex-CCD diffractometer
equipped with graphite monochromatic Mo-Kα radiation (λ = 0.71073 Ǻ) at 100(2) K1.A
multi-scan correction was applied. The structure was solved by the direct methods using
SIR-92 and refined by full-matrix least-squares refinement techniques on F2 using
SHELXL972. The hydrogen atoms were placed into the calculated positions and included in
the last cycles of the refinement. All calculations were done using Wingx software package3.
3
Table 1. Crystal data collection and structure refinement parameters for 4b Compound 4b Empirical formula Formula weight
C19H14N2 270.32
Temperature 293(2) K Wavelength 0.71073 Å Crystal system Monoclinic Space group P 21/c A 13.739(5)Å B 5.908(5)Å C 17.319(5)Å α (°) 90.000(5)°
β (°) 91.208(5)°
γ (°) 90.000(5)° Volume 1405.5(14) Å3
Z 4 Density (calculated) 1.278 Mg/m3
Absorption coefficient 0.076 mm-1
F(000) 568 Crystal size 0.20 x 0.19 x 0.17 mm3
Theta range for data collection 3.64 to 25.00° Index ranges -16 ≤ h ≤ 16, -7 ≤ k ≤ 7, -20 ≤ l ≤ 20 Reflections collected 15507 Independent reflections 2465 [R(int) = 0.0390] Completeness to theta = 25.00° 99.8 % Absorption correction Multi-scan Max. and min. transmission 0.9872 and 0.9850 Refinement method Full-matrix least-squares on F2
Data / restraints / parameters 2465 / 0 / 190 Goodness-of-fit on F2 1.038 Final R indices [I>2sigma(I)]a, b R1 = 0.0514, wR2 = 0.1235 R indices (all data) R1 = 0.0823, wR2 = 0.1365 Largest diff. peak and hole 0.168 and -0.149e.Å-3
aR = ∑(║Fo│– │Fc║)/∑│Fo│; bwR = {∑[w(Fo2 ─ Fc
2)2]/∑[w(Fo2)2]}1/2
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References 1. a) SMART: Bruker Molecular Analysis Research Tool, version 5.618. Bruker Analytical
X-ray System, 2000. b) SAINT-NT, version 6.45, Bruker Analytical X-Ray System, 2003. c)
SHELXTL-NT, version 6.10, Bruker Analytical X-ray System, 2000.
2. G. M. Sheldrick, Acta Cryst., 2008, A64, 112-122.
3. L. J. Farrugia, WinGX Version 1.80.05, An integrated system of Windows Programs for
the Solution, Refinement and Analysis of Single Crystal X-Ray Diffraction Data;
Department of Chemistry, University of Glasgow (1997-2009).
5
Copies of 1H NMR, 13C NMR
and HRMS
6
1H NMR
3-Phenylbenzo[b][1,6]naphthyridine (4a)
7
13C NMR
3-Phenylbenzo[b][1,6]naphthyridine (4a)
8
HRMS
3-Phenylbenzo[b][1,6]naphthyridine (4a)
+TOF MS: 0.865 to 0.998 min from Sample 1 (TuneSampleID) of 50005.wiffa=3.60979190650730920e-004, t0=-6.01277179989930400e+000 (Turbo Spray)
Max. 3883.3 counts.
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
0
200
400
600
800
1000
1200
1400
1600
1800
2000
2200
2400
2600
2800
3000
3200
3400
3600
3800
Inte
nsity
, cou
nts
256.0999
9
1H NMR
3-(p-Tolyl)benzo[b][1,6]naphthyridine (4b)
10
13C NMR
3-(p-Tolyl)benzo[b][1,6]naphthyridine (4b)
11
HRMS
3-(p-Tolyl)benzo[b][1,6]naphthyridine (4b)
+TOF MS: 1.164 to 1.348 min from Sample 1 (TuneSampleID) of 50006.wiffa=3.70725077892111030e-004, t0=-6.01277179989930400e+000 (Turbo Spray)
Max. 3968.1 counts.
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
0
200
400
600
800
1000
1200
1400
1600
1800
2000
2200
2400
2600
2800
3000
3200
3400
3600
3800
3968
Inte
nsity
, cou
nts
270.1156
12
1H NMR
3-(4-Butylphenyl)benzo[b][1,6]naphthyridine (4c)
13
13C NMR
3-(4-Butylphenyl)benzo[b][1,6]naphthyridine (4c)
14
HRMS
3-(4-Butylphenyl)benzo[b][1,6]naphthyridine (4c) +TOF MS: 1.514 to 1.597 min from Sample 1 (TuneSampleID) of 017.wiffa=3.43970586567407740e-004, t0=-6.01277179989930400e+000 (Turbo Spray)
Max. 2713.3 counts.
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
100
200
300
400
500
600
700
800
900
1000
1100
1200
1300
1400
1500
1600
1700
1800
1900
2000
2100
2200
2300
2400
2500
2600
2700
Inte
nsity
, cou
nts
312.1625
15
1H NMR
3-(Thiophen-3-yl)benzo[b][1,6]naphthyridine (4d)
16
13C NMR
3-(Thiophen-3-yl)benzo[b][1,6]naphthyridine (4d)
17
HRMS
3-(Thiophen-3-yl)benzo[b][1,6]naphthyridine (4d)
+TOF MS: 0.881 to 0.948 min from Sample 1 (TuneSampleID) of 50004.wiffa=3.65152765311198520e-004, t0=-6.01277179989930310e+000 (Turbo Spray)
Max. 4317.0 counts.
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
0
200
400
600
800
1000
1200
1400
1600
1800
2000
2200
2400
2600
2800
3000
3200
3400
3600
3800
4000
42004317
Inte
nsity
, cou
nts
262.0565
18
1H NMR
8-Methyl-3-(p-tolyl)benzo[b][1,6]naphthyridine (4e)
19
13C NMR
8-Methyl-3-(p-tolyl)benzo[b][1,6]naphthyridine (4e)
20
HRMS
8-Methyl-3-(p-tolyl)benzo[b][1,6]naphthyridine (4e)
+TOF MS: 1.014 to 1.098 min from Sample 1 (TuneSampleID) of 500015.wiffa=3.39822108975433210e-004, t0=-6.01277179989930400e+000 (Turbo Spray)
Max. 5339.3 counts.
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
0
200
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600
800
1000
1200
1400
1600
1800
2000
2200
2400
2600
2800
3000
3200
3400
3600
3800
4000
4200
4400
4600
4800
5000
52005339
Inte
nsity
, cou
nts
284.1313
21
1H NMR
3-(4-Ethylphenyl)-8-methylbenzo[b][1,6]naphthyridine (4f)
22
13C NMR
3-(4-Ethylphenyl)-8-methylbenzo[b][1,6]naphthyridine (4f)
23
HRMS
3-(4-Ethylphenyl)-8-methylbenzo[b][1,6]naphthyridine (4f)
+TOF MS: 0.781 to 1.131 min from Sample 1 (TuneSampleID) of 500014.wiffa=3.48102545163860160e-004, t0=-6.01277179989930130e+000 (Turbo Spray)
Max. 6265.2 counts.
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
0
500
1000
1500
2000
2500
3000
3500
4000
4500
5000
5500
6000
6265
Inte
nsity
, cou
nts
298.1471
24
1H NMR
8-Methoxy-3-phenylbenzo[b][1,6]naphthyridine (4g)
25
13C NMR
8-Methoxy-3-phenylbenzo[b][1,6]naphthyridine (4g)
26
HRMS
8-Methoxy-3-phenylbenzo[b][1,6]naphthyridine (4g)
+TOF MS: 0.931 to 1.064 min from Sample 1 (TuneSampleID) of 50007.wiffa=3.81543721165322690e-004, t0=-6.01277179989930400e+000 (Turbo Spray)
Max. 3872.4 counts.
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
0
200
400
600
800
1000
1200
1400
1600
1800
2000
2200
2400
2600
2800
3000
3200
3400
3600
3800
Inte
nsity
, cou
nts
286.1105
27
1H NMR
3-(4-(t-Butyl)phenyl)-8-methoxybenzo[b][1,6]naphthyridine (4h)
28
13C NMR
3-(4-(t-Butyl)phenyl)-8-methoxybenzo[b][1,6]naphthyridine (4h)
29
HRMS
3-(4-(t-Butyl)phenyl)-8-methoxybenzo[b][1,6]naphthyridine (4h) +TOF MS: 0.681 to 0.798 min from Sample 1 (TuneSampleID) of 005.wiffa=3.60125578360809970e-004, t0=-6.01277179989930400e+000 (Turbo Spray)
Max. 2263.5 counts.
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
0
100
200
300
400
500
600
700
800
900
1000
1100
1200
1300
1400
1500
1600
1700
1800
1900
2000
2100
22002264
Inte
nsity
, cou
nts
342.1732
30
1H NMR
7-(4-(Tert-butyl)phenyl)-1,6-naphthyridine (4i)
31
13C NMR
7-(4-(Tert-butyl)phenyl)-1,6-naphthyridine (4i)
32
HRMS
7-(4-(Tert-butyl)phenyl)-1,6-naphthyridine (4i)
+TOF MS: 0.831 to 0.881 min from Sample 1 (TuneSampleID) of 500021.wiffa=3.26410503500352640e-004, t0=-6.01277179989930310e+000 (Turbo Spray)
Max. 377.8 counts.
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
0
20
40
60
80
100
120
140
160
180
200
220
240
260
280
300
320
340
360
378
Inte
nsity
, cou
nts
262.1470
33
1H NMR
5-Methyl-3-phenyl-5H-pyrido[4,3-b]indole (6a)
34
13C NMR
5-methyl-3-phenyl-5H-pyrido[4,3-b]indole (6a)
35
HRMS
5-methyl-3-phenyl-5H-pyrido[4,3-b]indole (6a)
+TOF MS: 0.698 to 0.798 min from Sample 1 of r10.wiffa=3.40951955889840250e-004, t0=-6.01277179989930400e+000 (Turbo Spray)
Max. 1421.6 counts.
200 220 240 260 280 300 320 340 360 380 400 420 440 460 480m/z, Da
0
100
200
300
400
500
600
700
800
900
1000
1100
1200
1300
1400
Inte
nsity
, cou
nts
258.1156
36
1H NMR
5-Methyl-3-(p-tolyl)-5H-pyrido[4,3-b]indole (6b)
37
13C NMR
5-Methyl-3-(p-tolyl)-5H-pyrido[4,3-b]indole (6b)
38
HRMS
5-Methyl-3-(p-tolyl)-5H-pyrido[4,3-b]indole (6b)
+TOF MS: 1.930 to 2.264 min from Sample 1 of r11.wiffa=3.50086004738864890e-004, t0=-6.01277179989930130e+000 (Turbo Spray)
Max. 1338.4 counts.
120 140 160 180 200 220 240 260 280 300 320 340 360 380 400 420 440 460 480m/z, Da
0
50
100
150
200
250
300
350
400
450
500
550
600
650
700
750
800
850
900
950
1000
1050
1100
1150
1200
1250
13001338
Inte
nsity
, cou
nts
272.1313
39
1H NMR
3-(4-Butylphenyl)-5-methyl-5H-pyrido[4,3-b]indole (6c)
40
13C NMR
3-(4-Butylphenyl)-5-methyl-5H-pyrido[4,3-b]indole (6c)
41
HRMS
3-(4-Butylphenyl)-5-methyl-5H-pyrido[4,3-b]indole (6c)
+TOF MS: 0.648 to 0.731 min from Sample 1 of 0028.wiffa=3.65464671698700430e-004, t0=-6.01277179989930400e+000 (Turbo Spray)
Max. 556.2 counts.
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
0
50
100
150
200
250
300
350
400
450
500
550
Inte
nsity
, cou
nts
314.1783
42
1H NMR
3-(4-Methoxyphenyl)-5-methyl-5H-pyrido[4,3-b]indole (6d)
43
13C NMR
3-(4-Methoxyphenyl)-5-methyl-5H-pyrido[4,3-b]indole (6d)
44
HRMS
3-(4-Methoxyphenyl)-5-methyl-5H-pyrido[4,3-b]indole (6d)
45
1H NMR
5-Methyl-3-(thiophen-3-yl)-5H-pyrido[4,3-b]indole (6e)
46
13C NMR
5-Methyl-3-(thiophen-3-yl)-5H-pyrido[4,3-b]indole (6e)
47
HRMS
5-Methyl-3-(thiophen-3-yl)-5H-pyrido[4,3-b]indole (6e)
+TOF MS: 0.581 to 0.665 min from Sample 1 of 0030.wiffa=3.35056034768423410e-004, t0=-6.01277179989930400e+000 (Turbo Spray)
Max. 343.0 counts.
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
0
20
40
60
80
100
120
140
160
180
200
220
240
260
280
300
320
340
Inte
nsity
, cou
nts
264.0721
48
1H NMR
5-Methyl-3-(4-(trifluoromethyl)phenyl)-5H-pyrido[4,3-b]indole (6f)
49
13C NMR
5-Methyl-3-(4-(trifluoromethyl)phenyl)-5H-pyrido[4,3-b]indole (6f)
50
HRMS
5-Methyl-3-(4-(trifluoromethyl)phenyl)-5H-pyrido[4,3-b]indole (6f)
+TOF MS: 2.364 to 2.447 min from Sample 1 of 0029.wiffa=3.72335258482532690e-004, t0=-6.01277179989930400e+000 (Turbo Spray)
Max. 434.3 counts.
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
0
20
40
60
80
100
120
140
160
180
200
220
240
260
280
300
320
340
360
380
400
420434
Inte
nsity
, cou
nts
326.1030
51
1H NMR
5-Methyl-3-phenethyl-5H-pyrido[4,3-b]indole (6g)
52
13C NMR
5-Methyl-3-phenethyl-5H-pyrido[4,3-b]indole (6g)
53
HRMS
5-Methyl-3-phenethyl-5H-pyrido[4,3-b]indole (6g)
54
1H NMR
3-Cyclopropyl-5-methyl-5H-pyrido[4,3-b]indole (6h)
55
13C NMR
3-Cyclopropyl-5-methyl-5H-pyrido[4,3-b]indole (6h)
56
HRMS
3-Cyclopropyl-5-methyl-5H-pyrido[4,3-b]indole (6h)
57
1H NMR
3-Butyl-5-methyl-5H-pyrido[4,3-b]indole (6i)
58
13C NMR
3-Butyl-5-methyl-5H-pyrido[4,3-b]indole (6i)
59
HRMS
3-Butyl-5-methyl-5H-pyrido[4,3-b]indole (6i)
60
1H NMR
3-Phenylisoquinoline (8a)
61
13C NMR
3-Phenylisoquinoline (8a)
62
HRMS
3-Phenylisoquinoline (8a)
63
1H NMR
3-(4-Ethylphenyl)isoquinoline (8b)
64
13C NMR
3-(4-Ethylphenyl)isoquinoline (8b)
65
HRMS
3-(4-Ethylphenyl)isoquinoline (8b)
+TOF MS: 0.548 to 0.648 min from Sample 1 of 026.wiffa=4.20500719729197600e-004, t0=-5.66662779057200530e+003 (Turbo Spray)
Max. 1445.0 counts.
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
0
100
200
300
400
500
600
700
800
900
1000
1100
1200
1300
14001445 233.1205
66
1H NMR
3-(3-Methoxyphenyl)isoquinoline (8c)
67
13C NMR
3-(3-Methoxyphenyl)isoquinoline (8c)
68
HRMS
3-(3-Methoxyphenyl)isoquinoline (8c)
pa=4.22276555449639430e-004, t0=-5.66662779057200530e+003 (Turbo Spray)
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
0
50
100
150
200
250
300
350
400
450
500
550
600
650
700
750
800
850
900
950
1000
1050
1100
1150
1200
1250235.0998
69
1H NMR
3-(4-(Trifluoromethyl)phenyl)isoquinoline (8d)
70
13C NMR
3-(4-(Trifluoromethyl)phenyl)isoquinoline (8d)
71
HRMS
3-(4-(Trifluoromethyl)phenyl)isoquinoline (8d)
+TOF MS: 0.831 to 1.048 min from Sample 1 of 024.wiffa=4.55124927316336130e-004, t0=-5.66662779057200530e+003 (Turbo Spray)
Max. 1642.9 counts.
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
0
100
200
300
400
500
600
700
800
900
1000
1100
1200
1300
1400
1500
16001643 273.0765
72
1H NMR
7-(4-Butylphenyl)-[1,3]dioxolo[4,5-g]isoquinoline (8e)
73
13C NMR
7-(4-Butylphenyl)-[1,3]dioxolo[4,5-g]isoquinoline (8e)
74
HRMS
7-(4-Butylphenyl)-[1,3]dioxolo[4,5-g]isoquinoline (8e)
75
1H NMR
4-([1,3]Dioxolo[4,5-g]isoquinolin-7-yl)-N,N-dimethylaniline (8f)
76
13C NMR
4-([1,3]Dioxolo[4,5-g]isoquinolin-7-yl)-N,N-dimethylaniline (8f)
77
HRMS
4-([1,3]Dioxolo[4,5-g]isoquinolin-7-yl)-N,N-dimethylaniline (8f)
78
1H NMR
7-(4-(Trifluoromethyl)phenyl)-[1,3]dioxolo[4,5-g]isoquinoline (8g)
79
13C NMR
7-(4-(Trifluoromethyl)phenyl)-[1,3]dioxolo[4,5-g]isoquinoline (8g)
80
HRMS
7-(4-(Trifluoromethyl)phenyl)-[1,3]dioxolo[4,5-g]isoquinoline (8g)
81
1H NMR
3-Phenylbenzo[4,5]thieno[2,3-c]pyridine (10a)
82
13C NMR
3-Phenylbenzo[4,5]thieno[2,3-c]pyridine (10a)
83
HRMS
3-Phenylbenzo[4,5]thieno[2,3-c]pyridine (10a)
+TOF MS: 1.114 to 1.681 min from Sample 1 (TuneSampleID) of 500020.wiffa=3.25733870246915740e-004, t0=-6.01277179989930040e+000 (Turbo Spray)
Max. 6316.4 counts.
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
0
500
1000
1500
2000
2500
3000
3500
4000
4500
5000
5500
6000
6316
Inte
nsity
, cou
nts
261.0612
84
1H NMR
3-(p-Tolyl)benzo[4,5]thieno[2,3-c]pyridine (10b)
85
13C NMR
3-(p-Tolyl)benzo[4,5]thieno[2,3-c]pyridine (10b)
86
HRMS
3-(p-Tolyl)benzo[4,5]thieno[2,3-c]pyridine (10b)
+TOF MS: 1.098 to 2.230 min from Sample 1 (TuneSampleID) of 500019.wiffa=3.34363514946097870e-004, t0=-6.01277179989930930e+000 (Turbo Spray)
Max. 5878.2 counts.
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
500
1000
1500
2000
2500
3000
3500
4000
4500
5000
5500
5878
Inte
nsity
, cou
nts
275.0769
87
1H NMR
3-(Thiophen-3-yl)benzo[4,5]thieno[2,3-c]pyridine (10c)
88
13C NMR
3-(Thiophen-3-yl)benzo[4,5]thieno[2,3-c]pyridine (10c)
89
HRMS
3-(Thiophen-3-yl)benzo[4,5]thieno[2,3-c]pyridine (10c)
+TOF MS: 0.581 to 1.031 min from Sample 1 (TuneSampleID) of 500018.wiffa=3.29428764599176060e-004, t0=-6.01277179989930040e+000 (Turbo Spray)
Max. 5751.2 counts.
240 260 280 300 320 340 360 380 400 420 440 460 480 500 520 540 560 580 600 620 640 660 680m/z, Da
500
1000
1500
2000
2500
3000
3500
4000
4500
5000
5500
5751
Inte
nsity
, cou
nts
267.0176
90
1H NMR
3-(4-(Trifluoromethyl)phenyl)benzo[4,5]thieno[2,3-c]pyridine(10d)
91
13C NMR
3-(4-(Trifluoromethyl)phenyl)benzo[4,5]thieno[2,3-c]pyridine(10d)
92
13C NMR
3-(4-(Trifluoromethyl)phenyl)benzo[4,5]thieno[2,3-c]pyridine(10d)
+TOF MS: 0.615 to 0.815 min from Sample 1 (TuneSampleID) of 500012.wiffa=3.65697788666145250e-004, t0=-6.01277179989930310e+000 (Turbo Spray)
Max. 6056.9 counts.
100 150 200 250 300 350 400 450 500 550 600 650 700 750 800 850 900 950 1000m/z, Da
0
500
1000
1500
2000
2500
3000
3500
4000
4500
5000
5500
6000
Inte
nsity
, cou
nts
329.0487
93
1H NMR
3-Phenylbenzofuro[3,2-c]pyridine (12a)
94
13C NMR
3-Phenylbenzofuro[3,2-c]pyridine (12a)
95
HRMS
3-Phenylbenzofuro[3,2-c]pyridine (12a)
96
1H NMR
3-(4-(Tert-butyl)phenyl)benzofuro[3,2-c]pyridine (12b)
97
13C NMR
3-(4-(Tert-butyl)phenyl)benzofuro[3,2-c]pyridine (12b)
98
HRMS
3-(4-(Tert-butyl)phenyl)benzofuro[3,2-c]pyridine (12b)
99
1H NMR
3-(3-Methoxyphenyl)benzofuro[3,2-c]pyridine (12c)
100
13C NMR
3-(3-Methoxyphenyl)benzofuro[3,2-c]pyridine (12c)
101
HRMS
3-(3-Methoxyphenyl)benzofuro[3,2-c]pyridine (12c)
102
1HNMR
3-(4-(Trifluoromethoxy)phenyl)benzofuro[3,2-c]pyridine (12d)
103
13C NMR
3-(4-(Trifluoromethoxy)phenyl)benzofuro[3,2-c]pyridine (12d)
104
HRMS
3-(4-(Trifluoromethoxy)phenyl)benzofuro[3,2-c]pyridine (12d)