Indole → HCID 23118671, compound

HRID 1178730Notes

Reaction equation

HRID 1178730 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.[Cl:15][C:16]1[N:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19].[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26]1>>[Cl:15][C:16]1[C:17]([C:18]([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:19])=[CH:21][CH:22]=[CH:23][N:24]=1

Participants

4

Reactant 3

HCID 798IndoleHCID 9189PhenanthridineHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 23118671HCID 23118671, compound

Procedure

(2-Chloro-pyridin-3-yl)-[6-(1H-indol-3-yl)-6H-phenanthridin-5-yl]-methanone was prepared from phenanthridine, 2-chloronicotinoyl chloride, and indole according to GP 2. Yield, 55%. 1H-NMR (DMSO-d6): δ=6.18 (s, br., 1H), 6.37 (d, J=7.9 Hz, 1H), 6.79 (t, J≈7 Hz, 1H), 7.01-7.17 (m, 4H), 7.23-7.30 (m, 1H), 7.36-7.62 (m, 5H), 7.88 (s, br., 1H), 7.94 (d, J=7.7 Hz, 1H), 8.07 (d, J=7.1 Hz, 1H), 8.37 (d, J=4.6 Hz, J=1.3 Hz, 1H), 10.72 (s, 1H); (+)-ESI-MS: m/z=436 [M(35Cl)+H]+, 319 [M(35Cl)-indole+H]+.

Workup

  1. customYield

Sources & evidence

ORD record
ord-dcc98cc5f9e840fca0bbc4fe2e1bc607
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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