Indole → HCID 23118680, compound

HRID 1178725Notes

Reaction equation

HRID 1178725 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]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19].[NH:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27]1>>[F:15][C:16]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:17]=1[C:18]([N:6]1[CH:7]([C:28]2[C:29]3[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=3)[NH:26][CH:27]=2)[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2)=[O:19]

Participants

4

Reactant 3

HCID 798IndoleHCID 9189PhenanthridineHCID 5880812,4-Difluorobenzoyl chloride

Product 1

HCID 23118680HCID 23118680, compound

Procedure

(2,4-Difluoro-phenyl)-[6-(1H-indol-3-yl)-6H-phenanthridin-5-yl]-methanone was prepared from phenanthridine, 2,4-difluorobenzoyl chloride, and indole according to GP 2. Yield, 25%. 1H-NMR (DMSO-d6): δ=6.18 (d, br., J=1.4 Hz, 1H), 6.34 (d, br., J≈5 Hz, 1H), 6.82 (t, J≈7 Hz, 1H), 6.99-7.18 (m, 5H), 7.23-7.28 (m, 1H), 7.32 (s, br., 1H), 7.39-7.59 (m, 4H), 7.85 (s, br., 1H), 7.94 (dd, J=7.9 Hz, J=1.2 Hz, 1H), 8.07 (d, J=7.6 Hz, 1H), 10.71 (s, 1H); (+)-ESI-MS: m/z=437 [M+H]+, 320 [M-indole+H]+.

Workup

  1. customYield

Sources & evidence

ORD record
ord-311c07de0d3b4060bfd1a3b26820955b
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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