SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 3, 2009, Pages 433-436

Unexpected C2-arylation of 1-(pyridin-2-yl)indole-3-carboxaldehyde mediated by copper

(3) Sagnes, Charlène a Fournet, Guy a Joseph, Benoît a

a UNIVERSITÉ LYON 1 (France)

Author keywords

Arylation; Copper; Indole; Pyridine

Indexed keywords

EID: 62249091058 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087549 Document Type: Article

Times cited : (17)

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- Analytical Data of 1-(Pyridin-2-yl)-1H-indole-3- carboxaldehyde (2a) Mp 114-115 °C (MeOH, IR (KBr, 3101, 3050, 2821, 1667, 1649, 1593, 1579, 1539, 1471, 1455, 1444, 1224, 1128, 1083, 739 cm -1. 1H NMR (300 MHz, CDCl3, δ, 7.33-7.43 (m, 3 H, H-5, H-5′, H-6, 7.64 (d, 1 H, J, 8.3 Hz, H-3′, 7.95 (td, 1 H, J, 1.9, 7.7 Hz, H-4′, 8.02-8.05 (m, 1 H, H-4 or H-7, 8.38 (s, 1 H, H-2, 8.38-8.41 (m, 1 H, H-4 or H-7, 8.64 (dd, 1 H, J, 1.3, 4.7 Hz, H-6′, 10.16 (s, 1 H, CHO, 13C NMR (75 MHz, CDCl3, δ, 112.8 (CH, 115.7 (CH, 120.5 (C, 122.2 (CH, 122.3 (CH, 123.8 (CH, 125.1 (CH, 126.3 (C, 136.2 (C, 137.0 (CH, 139.0 (CH, 149.4 (CH, 150.9 (C, 185.4 CO, ESI-MS: m/z, 223 [M, H, Anal. Calcd for C14H10N2O: C, 75.66; H, 4.54; N, 12.60. Found: C, 75.99; H, 4.32; N, 12.55
- 2O: C, 75.66; H, 4.54; N, 12.60. Found: C, 75.99; H, 4.32; N, 12.55.

20
- 62249167770
- Analytical Data of 1,2-Di(pyridin-2-yl)-1H-indole-3- carboxaldehyde (3a) Mp 127-128 °C (EtOAc-PE, IR (KBr, 3051, 3012, 2831, 1648, 1443, 1387, 1050, 754, 741 cm-1. 1H NMR (300 MHz, CDCl3, δ, 7.19 (d, 1 H, J, 7.9 Hz, H-3′ or H-3″, 7.27-7.44 (m, 5 H, H-3′ or H-3″, H-5, H-5′, H-5″, H-6, 7.54 (d, 1 H, J, 7,4 Hz, H-4 or H-7, 7.67-7.79 (m, 2 H, H-4′, H-4″, 8.53-8.60 (m, 3 H, H-4 or H-7, H-6′, H-6″, 10.18 (s, 1 H, CHO, 13C NMR (75 MHz, CDCl3, δ, 111.4 (CH, 117.7 (C, 122.1 (CH, 122.7 (CH, 123.1 (CH, 123.6 (CH, 124.0 (CH, 125.3 (CH, 125.4 (C, 126.8 (CH, 136.3 (CH, 137.4 (C, 138.4 (CH, 147.3 (C, 148.8 (C, 149.6 (CH, 149.9 (CH, 150.4 (C, 187.8 CO, ESI-MS: m/z, 300 [M, H, Anal. Calcd for C 19H13N3O: C, 76.24; H, 4.38; N, 14.04. Found: C, 76.34;
- 3O: C, 76.24; H, 4.38; N, 14.04. Found: C, 76.34; H, 4.43; N, 13.96.

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22
- 62249111101
- 4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography (PE-EtOAc, 2:8 to 1:1) to provide 3a (110 mg, 84%).
- 4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography (PE-EtOAc, 2:8 to 1:1) to provide 3a (110 mg, 84%).

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33
- 62249139159
- Analytical Data of 2-Phenyl-1-(pyridin-2-yl)-1H-indole-3-carboxaldehyde (3b)26 Mp 171-172 °C (EtOAc-PE, IR (KBr, 3065, 3043, 2836, 1652, 1466, 1454, 1384, 1225, 1082, 756 cm-1. 1H NMR (300 MHz, CDCl3, δ, 6.94 (d, 1 H, J, 7.9 Hz, H-3′, 7.30-7.43 (m, 8 H, H-5, H-5′, H-6, Harom, 7.51 (d, 1 H, J, 7.5 Hz, H-4 or H-7, 7.68 (td, 1 H, J, 1.9, 8.0 Hz, H-4′, 8.50 (br d, 1 H, J, 6.9 Hz, H-4 or H-7, 8.65 (dd, 1 H, J, 1.3, 4.9 Hz, H-6′, 9.97 (s, 1 H, CHO, 13C NMR (75 MHz, CDCl3, δ, 111.6 (CH, 116.9 (C, 122.2 (CH, 122.4 (CH, 123.2 (CH, 123.9 (CH, 124.8 (CH, 125.5 (C, 128.5 (2 CH, 128.8 (C, 129.5 (CH, 131.1 (2 CH, 137.5 (C, 138.3 (CH, 149.6 (CH, 149.9 (C, 150.2 (C, 187.6 CO, ESI-MS: m/z, 299 [M, H, Anal. Calcd for C20H14N2O: C 80.52; H
- 2O: C 80.52; H, 4.73; N, 9.39. Found: C, 80.83; H, 4.85; N, 9.27.

34
- 62249213935
- Analytical Data of 1-(Pyridin-2-yl)-2-(4-methylphenyl)-1 H-indole-3-carboxaldehyde (3f) Mp 206-207 °C (EtOAc-PE, IR (KBr, 3048, 2916, 2836, 1642, 1435, 1081, 747, 737 cm-1. 1H NMR (300 MHz, CDCl3, δ, 2.37 (s, 3 H, CH 3, 6.92 (d, 1 H, J, 6.9 Hz, H-3′, 7.15 (d, 2 H, J, 8.0 Hz, Harom, 7.26 (d, 2 H, J, 8.0 Hz, H arom, 7.29-7.41 (m, 3 H, H-5, H-5′, H-6, 7.50 (dd, 1 H, J, 0.9, 7.4 Hz, H-4 or H-7, 7.68 (td, 1 H, J, 1.9, 7.7 Hz, H-4′, 8.48 (dd, 1 H, J, 1.1, 7.3 Hz, H-4 or H-7, 8.65 (dd, 1 H, J, 1.1, 4.9 Hz, H-6′, 9.95 (s, 1 H, CHO, 13C NMR (75 MHz, CDCl3, δ, 21.4 (CH3, 111.5 (CH, 116.7 (C, 122.1 (CH, 122.5 (CH, 123.1 (CH, 123.8 (CH, 124.7 (CH, 125.5 (C, 125.8 (C, 129.2 (2 CH, 131.0 (2 CH, 137.5 (C, 138.3 (CH, 139.7 (C, 149.6 (CH, 150.2 C, 150.3
- 2O: C, 80.75, H, 5.16; N, 8.97. Found: C, 8.48; H, 4.97; N, 9.03.

35
- 34548391350
- Kantam, M. L.; Yadav, J.; Laha, S.; Sreedhar, B.; Jha, S. Adv. Synth. Catal. 2007, 349, 1938.
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- Kantam, M.L.¹ Yadav, J.² Laha, S.³ Sreedhar, B.⁴ Jha, S.⁵

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- (1987) Heterocycles , vol.26 , pp. 3101
- Seki, K.¹ Ohkura, K.² Terashima, M.³ Kanaoka, Y.⁴

37
- 62249164797
- Analytical Data of 1-(Pyridin-2-yl)-1H-indole-3- carbonitrile (11e) Mp 150-151 °C (MeOH, IR (KBr, 3135, 3050, 2222, 1592, 1540, 1473, 1455, 1434, 1229, 1095, 735 cm-1. 1H NMR (300 MHz, CDCl3, δ, 7.32-7.45 (m, 3 H, H-5, H-5′, H-6, 7.56 (d, 1 H, J, 8.1 Hz, H-3′, 7.83 (br d, 1 H, J, 7.5 Hz, H-4 or H-7, 7.93 (td, 1 H, J, 1.9, 7.5 Hz, H-4′, 8.10 (br d, 1 H, J, 7.1 Hz, H-4 or H-7, 8.23 (s, 1 H, H-2, 8.63 (dd, 1 H, J, 1.1, 4.9 Hz, H-6′, 13C NMR (75 MHz, CDCl 3, δ, 89.8 (C, 113.4 (CH, 115.3 (C, 115.6 (CH, 120.0 (CH, 122.3 (CH, 123.4 (CH, 125.2 (CH, 128.7 (C, 133.3 (CH, 134.4 (C, 139.1 (CH, 149.5 (CH, 150.7 C, ESIMS: m/z, 220 [M, H, Anal. Calcd for C14H9N3: C, 76.70, H, 4.14, N, 19.17. Found: C, 76.72; H, 4.08; N, 19.25
- 3: C, 76.70, H, 4.14, N, 19.17. Found: C, 76.72; H, 4.08; N, 19.25.

38
- 62249087567
- Analytical Data of 1,2-Di(pyridin-2-yl)-1H-indole-3- carbonitrile (11d) Mp 128-129 °C (CH2Cl2-PE, IR (KBr, 3065, 2213, 1589, 1569, 1467, 1448, 1435, 1393, 1225, 738 cm -1. 1H NMR (300 MHz, CDCl3, δ, 7.24-7.41 (m, 5 H, H-3′ or H-3″, H-5, H-5′, H-5″, H-6, 7.50-7.53 (m, 1 H, H-4 or H-7, 7.82-7.89 (m, 4 H, H-3′ or H-3″, H-4 or H-7, H-4′, H-4″, 8.44 (br d, 1 H, J, 4.1 Hz, H-6′or H-6″, 8.51 (dd, 1 H, J, 1.1, 4.7, H-6′ or H-6″, 13C NMR (75 MHz, CDCl3, δ, 89.3 (C, 112.1 (CH, 116.1 (C, 120.0 (CH, 122.0 (CH, 123.1 (CH, 123.4 (CH, 123.5 (CH, 124.9 (CH, 125.5 (CH, 127.6 (C, 136.8 (CH, 137.2 (C, 138.4 (CH, 144.8 (C, 148.2 (C, 149.5 (CH, 149.6 (CH, 150.7 C, ESI-MS: m/z, 297 [M, H, Anal. Calcd for C19H12N 4: C, 77.0
- 4: C, 77.01, H, 4.08, N, 18.91. Found: C, 76.88; H, 4.27; N, 19.01.

39
- 62249165524
- Typical Procedure In a microwave vial with a magnetic stir bar was introduced indole-3-carboxaldehyde (100 mg, 0.68 mmol, 1 equiv, Cu 2O (10 mg, 0.07 mmol, 0.1 equiv, and K2CO3 (189 mg, 1.36 mmol, 2 equiv) in anhyd DMF (1.4 mL, After a purge with argon, 2-iodopyridine (153 μL, 1.36 mmol, 2 equiv) was added. The vial was sealed and heated at 240 °C under microwave irradiation (Biotage Initiator) for 1 h. The mixture was filtered through Celite, and the filtrate was concentrated in vacuo. The residue was diluted in EtOAc (20 mL, The organic layer was washed with a solution of 2.5% aq NH4OH (2 x 20 mL) and brine (20 mL, The organic phase was dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (PE-EtOAc, 2:8 to 1:1) to provide 2a (88 mg, 58, and 3a 73 mg, 36
- 4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (PE-EtOAc, 2:8 to 1:1) to provide 2a (88 mg, 58%) and 3a (73 mg, 36%).

40
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- Maassarani, F.¹ Pfeffer, M.² Spencer, J.³ Wehman, E.⁴

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