Indole → HCID 68490941, compound

HRID 1178728Notes

Reaction equation

HRID 1178728 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.[F:15][C:16]([F:28])([F:27])[O:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].[NH:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30]1>>[NH:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([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]=[CH:26][C:18]=2[O:17][C:16]([F:28])([F:27])[F:15])=[O:21])=[CH:30]1

Participants

4

Reactant 3

HCID 798IndoleHCID 9189PhenanthridineHCID 27772412-(Trifluoromethoxy)benzoyl Chloride

Product 1

HCID 68490941HCID 68490941, compound

Procedure

[6-(1H-Indol-3-yl)-6H-phenanthridin-5-yl]-(2-trifluoromethoxy-phenyl)-methanone was prepared from phenanthridine, 2-(trifluoromethoxy)benzoyl chloride, and indole according to GP 2. Yield, 31%. 1H-NMR (DMSO-d6): δ=6.16 (s, br., 1H), 6.25 (d, J=7.9 Hz, 1H), 6.72 (t, J=7.6 Hz, 1H), 7.00-7.12 (m, 4H), 7.23-7.29 (m, 1H), 7.36 (s, br., 1H), 7.37-7.59 (m, 6H), 7.85-7.95 (m, 2H), 8.05 (d, J=7.5 Hz, 1H), 10.68 (s, 1H); (+)-ESI-MS: m/z=485 [M+H]+, 368 [M-indole+H]+; (−)-ESI-MS: m/z=483 (M−H)−.

Workup

  1. customYield

Sources & evidence

ORD record
ord-20dc8c6160f148378d899715d37c8b6e
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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