Indole → HCID 68492233, compound

HRID 1178722Notes

Reaction equation

HRID 1178722 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.[Br: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>>[Br: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

4

Reactant 3

HCID 798IndoleHCID 9189PhenanthridineHCID 74377Benzoyl chloride, 3-bromo-

Product 1

HCID 68492233HCID 68492233, compound

Procedure

(3-Bromo-phenyl)-[6-(1H-indol-3-yl)-6H-phenanthridin-5-yl]-methanone was prepared from phenanthridine, 3-bromobenzoyl chloride, and indole according to GP 2. Yield, 22%. 1H-NMR (DMSO-d6): δ=6.22 (d, J=1.9 Hz, 1H), 6.41 (s, br., 1H), 6.86 (t, J=7.5 Hz, 1H), 6.99-7.28 (m, 7H), 7.40-7.48 (m, 2H), 7.51-7.60 (m, 3H), 7.84 (“d”, J=7 Hz, 1H), 7.98 (dd, J=7.9 Hz, J=1.1 Hz, 1H), 8.12 (d, J=7.5 Hz, 1H), 10.71 (s, 1H); (+)-ESI-MS: m/z=479 [M(79Br)+H]+, 362[M(79Br)-indole+H]+.

Workup

  1. customYield

Sources & evidence

ORD record
ord-833c017c3deb45509fb17e5fa2eb8ff5
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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