Indole → HCID 23118674, compound

HRID 1178729Notes

Reaction equation

HRID 1178729 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[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][N:17]=1.[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[N:17]=[CH:18][C:19]([C:20]([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:21])=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 798IndoleHCID 9189PhenanthridineHCID 27821656-Chloronicotinoyl Chloride

Product 1

HCID 23118674HCID 23118674, compound

Procedure

(6-Chloro-pyridin-3-yl)-[6-(1H-indol-3-yl)-6H-phenanthridin-5-yl]-methanone was prepared from phenanthridine, 6-chloronicotinoyl chloride, and indole according to GP 2. Yield, 55%. 1H-NMR (DMSO-d6): δ=6.24 (d, J=1.7 Hz, 1H), 6.46 (s, br., 1H), 6.90 (t, J=7.5 Hz, 1H), 6.99-7.09 (m, 2H), 7.15-7.28 (m, 3H), 7.40-7.48 (m, 2H), 7.51-7.59 (m, 2H), 7.64 (d, J=8.2 Hz, 1H), 7.85 (d, J≈7 Hz, 1H), 8.01 (d, J=7.6 Hz, 1H), 8.12 (d, J=7.6 Hz, 1H), 8.23 (s, 1H), 10.73 (s, 1H); (+)-ESI-MS: m/z=436 [M(35Cl)+H]+, 319 [M(35Cl)-indole+H]+.

Workup

  1. customYield

Sources & evidence

ORD record
ord-04751dc75ba54e7c830c847e81ec4ae6
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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