Indole → HCID 23118688, compound

HRID 1178733Notes

Reaction equation

HRID 1178733 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.[CH3:15][N:16]1[C:20]([C:21](Cl)=[O:22])=[CH:19][C:18]([CH3:24])=[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>>[CH3:15][N:16]1[C:20]([C:21]([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:22])=[CH:19][C:18]([CH3:24])=[N:17]1

Participants

4

Reactant 3

HCID 798IndoleHCID 9189PhenanthridineHCID 27362992,5-Dimethyl-2H-pyrazole-3-carbonyl chloride

Product 1

HCID 23118688HCID 23118688, compound

Procedure

(2,5-Dimethyl-2H-pyrazol-3-yl)-[6-(1H-indol-3-yl)-6H-phenanthridin-5-yl]-methanone was prepared from phenanthridine, 1,3-dimethylpyrazole-5-carbonyl chloride, and indole according to GP 2. Yield, 7%. 1H-NMR (DMSO-d6): δ=1.97 (s, 3H), 3.77 (s, 3H), 5.56 (s, 1H), 6.20 (s, 1H), 6.63 (s, br., 1H), 6.95 (t, J=7.5 Hz, 1H), 6.99-7.10 (m, 2H), 7.14-7.30 (m, 3H), 7.42 (t, J≈7.2 Hz, 1H), 7.49-7.58 (m, 2H), 7.83 (d, J=6.7 Hz, 1H), 7.98 (d, J=7.6 Hz, 1H), 8.09 (d, J=7.6 Hz, 1H), 10.72 (s, 1H); (+)-ESI-MS: m/z=419 [M+H]+, 302 [M-indole+H]+.

Workup

  1. customYield

Sources & evidence

ORD record
ord-1887e96316594818b6e23c52a99c0f31
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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