Indole → HCID 23118679, compound

HRID 1178721Notes

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:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=[O:20].[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26]1>>[F:15][C:16]1[CH:17]=[C:18]([C:19]([N:6]2[CH:7]([C:27]3[C:28]4[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=4)[NH:25][CH:26]=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:20])[CH:22]=[CH:23][CH:24]=1

Participants

Reactant 3

HCID 798Indole

HCID 9189Phenanthridine

HCID 743763-Fluorobenzoyl chloride

Product 1

HCID 23118679HCID 23118679, compound

Procedure

(3-Fluoro-phenyl)-[6-(1H-indol-3-yl)-6H-phenanthridin-5-yl]-methanone was prepared from phenanthridine, 3-fluorobenzoyl chloride, and indole according to GP 2. Yield, 41%. 1H-NMR (DMSO-d6): δ=6.21 (d, J=1.9 Hz, 1H), 6.41 (s, br., 1H), 6.84 (t, J=7.5 Hz, 1H), 6.96 (d, J=7.5 Hz, 1H), 6.99-7.11 (m, 3H), 7.14 (ddd, J=J=7.7 Hz, J=0.8 Hz, 1H), 7.17-7.35 (m, 4H), 7.43 (ddd, J=J=7.4 Hz, J=1.1 Hz, 1H), 7.54 (“t”, J=7.2 Hz, 2H), 7.85 (“d”, J=7 Hz, 1H), 7.97 (dd, J=7.9 Hz, J=1.2 Hz, 1H), 8.11 (d, J=7.5 Hz, 1H), 10.71 (s, br., 1H); (+)-ESI-MS: m/z=419 [M+H]+, 302 [M−indole+H]+.

Workup

customYield

Sources & evidence

ORD record: ord-9885ed55ee3e44b5935c31e203e76493
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07276606B2

Reaction notes

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