Indole → HCID 68491432, compound

HRID 1178724Notes

Reaction equation

HRID 1178724 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:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21](Cl)=[O:22].[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:21]([C:20]2[CH:24]=[CH:25][CH:26]=[C:18]([O:17][C:16]([F:28])([F:27])[F:15])[CH:19]=2)=[O:22])=[CH:30]1

Participants

4

Reactant 3

HCID 798IndoleHCID 9189PhenanthridineHCID 5228543-(Trifluoromethoxy)benzoyl chloride

Product 1

HCID 68491432HCID 68491432, compound

Procedure

[6-(1H-Indol-3-yl)-6H-phenanthridin-5-yl]-(3-trifluoromethoxy-phenyl)-methanone was prepared from phenanthridine, 3-(trifluoromethoxy)benzoyl chloride, and indole according to GP 2. Yield, 16%. 1H-NMR (DMSO-d6): δ=6.22 (d, J=2.0 Hz, 1H), 6.37 (s, br., 1H), 6.83 (t, J=7.5 Hz, 1H), 6.99-7.32 (m, 7H), 7.35-7.48 (m, 3H), 7.51-7.59 (m, 2H), 7.85 (“d”, J≈7 Hz, 1H), 7.98 (dd, J=7.8 Hz, J=1.0 Hz, 1H), 8.12 (d, J=7.6 Hz, 1H), 10.72 (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-c28695a0eb594b8690a7a476179da255
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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