Indole → HCID 68491408, compound

HRID 1178717Notes

Reaction equation

HRID 1178717 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.[C:15]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16].[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29]1>>[C:15]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([N:6]2[CH:7]([C:30]3[C:31]4[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=4)[NH:28][CH:29]=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:24])=[CH:21][CH:20]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 3

HCID 798IndoleHCID 9189PhenanthridineHCID 743724-tert-Butylbenzoyl chloride

Product 1

HCID 68491408HCID 68491408, compound

Procedure

(4-tert-Butyl-phenyl)-[6-(1H-indol-3-yl)-6H-phenanthridin-5-yl]-methanone was prepared from phenanthridine, 4-tert-butylbenzoyl chloride, and indole according to GP 2. Yield, 34%. 1H-NMR (DMSO-d6): δ=1.21 (s, 9 H), 6.20 (dd, J=2.5 Hz, J=0.8 Hz, 1H), 6.40 (d, br., J=7 Hz, 1H), 6.82 (t, J≈8 Hz, 1H), 6.99-7.08 (m, 2H), 7.11 (ddd, J=J=7.6 Hz, J=1.1 Hz, 1H), 7.14-7.19 (m, 3H), 7.22-7.27 (m, 1H), 7.30 (“d”, J≈8.6 Hz, 2H), 7.43 (ddd, J≈J≈7.5 Hz, J=1.2 Hz, 1H), 7.50-7.57 (m, 2H), 7.85-7.90 (m, 1H), 7.95 (dd, J=7.8 Hz, J=1.3 Hz, 1H), 8.09 (“d”, J≈7.5 Hz, 1H), 10.69 (s, 1H); (+)-ESI-MS: m/z=457 [M+H]+, 340 [M-indole+H]+.

Workup

  1. customYield

Sources & evidence

ORD record
ord-3ede21195e4647948d66550d382f16f3
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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