Indole → HCID 68487536, compound

HRID 1178723Notes

Reaction equation

HRID 1178723 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:27])([F:26])[C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20](Cl)=[O:21].[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29]1>>[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([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]([C:16]([F:27])([F:26])[F:15])[CH:18]=2)=[O:21])=[CH:29]1

Participants

4

Reactant 3

HCID 798IndoleHCID 9189PhenanthridineHCID 752573-(Trifluoromethyl)benzoyl chloride

Product 1

HCID 68487536HCID 68487536, compound

Procedure

[6-(1H-Indol-3-yl)-6H-phenanthridin-5-yl]-(3-trifluoromethyl-phenyl)-methanone was prepared from phenanthridine, 3-trifluoromethylbenzoyl chloride, and indole according to GP 2. Yield, 3%. 1H-NMR (DMSO-d6): δ=6.24 (d, J=1.9 Hz, 1H), 6.38 (s, br., 1H), 6.82 (t, J=7.5 Hz, 1H), 7.01-7.10 (m, 2H), 7.15 (t, J=7.6 Hz, 1H), 7.20-7.32 (m, 2H), 7.40-7.60 (m, 6H), 7.74 (d, J=7.3 Hz, 1H), 7.88 (d, br., J=7 Hz, 1H), 8.00 (d, J=7.6 Hz, 1H), 8.13 (d, J=7.6 Hz, 1H), 10.73 (s, 1H); (+)-ESI-MS: m/z=469 [M+H]+, 352 [M-indole+H]+; (−)-ESI-MS: m/z=467 (M−H)−.

Workup

  1. customYield

Sources & evidence

ORD record
ord-82763160c64f4afd855be9535f645c8b
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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