Indole → HCID 69423619, compound

HRID 1178720Notes

Reaction equation

HRID 1178720 reaction equation
[CH:1]1[C:14]2[C:5](=[N:6][CH:7]=[C:8]3[C:13]=2[CH:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=[CH:3][CH:2]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20](Cl)=[O:21].[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27]1>>[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([CH:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[N:6]2[C:20]([C:19]2[CH:23]=[CH:24][CH:25]=[C:17]([O:16][CH3:15])[CH:18]=2)=[O:21])=[CH:27]1

Participants

4

Reactant 3

HCID 798IndoleHCID 9189PhenanthridineHCID 74374m-Anisoyl chloride

Product 1

HCID 69423619HCID 69423619, compound

Procedure

[6-(1H-Indol-3-yl)-6H-phenanthridin-5-yl]-(3-methoxy-phenyl)-methanone was prepared from phenanthridine, 3-methoxybenzoyl chloride, and indole according to GP 2. Yield, 84%. 1H-NMR (CD3OD): δ=3.62 (s, 3H), 6.19 (s, 1H), 6.37 (s, br., 1H), 6.71-6.86 (m, 3H), 6.91 (dd, J=8.1 Hz, J=1.9 Hz, 1H), 7.02-7.26 (m, 5H), 7.32 (s, br., 1H), 7.39-7.48 (m, 2H), 7.54 (td, J=7.1 Hz, J=2.5 Hz, 1H), 7.90 (dd, J=7.9 Hz, J=1.2 Hz, 1H), 7.97 (s, br., 1H), 8.06 (d, J=7.8 Hz, 1H); (+)-ESI-MS: m/z=431 [M+H]+, 314 [M-indole+H]+.

Workup

  1. customYield

Sources & evidence

ORD record
ord-4168ff2eefd649149e2bf3bf2d26d416
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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