Indole → HCID 86602188, compound

HRID 1178726Notes

Reaction equation

HRID 1178726 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:31])([F:30])[C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[C:20](Cl)=[O:21].[NH:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33]1>>[F:15][C:16]([F:31])([F:30])[C:17]1[CH:18]=[C:19]([C:20]([N:6]2[CH:7]([C:34]3[C:35]4[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=4)[NH:32][CH:33]=3)[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]2=3)=[O:21])[CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1

Participants

4

Reactant 3

HCID 798IndoleHCID 9189PhenanthridineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chloride

Product 1

HCID 86602188HCID 86602188, compound

Procedure

(3,5-Bis-trifluoromethyl-phenyl)-[6-(1H-indol-3-yl)-6H-phenanthridin-5-yl]-methanone was prepared from phenanthridine, 3,5-bis(trifluoromethyl)benzoyl chloride, and indole according to GP 2. Yield, 8%. 1H-NMR (CD3OD): δ=6.22 (d, J=0.8 Hz, 1H), 6.29 (s, br., 1H), 6.79 (t, J=7.5 Hz, 1H), 7.05-7.14 (m, 2H), 7.16-7.27 (m, 2H), 7.37 (s, br., 1H), 7.42-7.52 (m, 2H), 7.58 (“t”, J≈7.3 Hz, 1H), 7.77 (s, br., 2H), 7.96 (s, br., 1H), 7.99 (dd, J=7.8 Hz, J=1.2 Hz, 2H), 8.12 (d, J=7.9 Hz, 1H); (+)-ESI-MS: m/z=537 [M+H]+, 420 [M-indole+H]+; (−)-ESI-MS: m/z=535 (M−H)−.

Workup

  1. customYield

Sources & evidence

ORD record
ord-a2114d58b0ea4d398fb2b6e2947fad6c
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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