Indole → HCID 23118668, compound

HRID 1178738Notes

Reaction equation

HRID 1178738 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.[CH:15]1([C:20](Cl)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16]1.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24]1>>[CH:15]1([C:20]([N:6]2[CH:7]([C:25]3[C:26]4[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=4)[NH:23][CH:24]=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])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 3

HCID 798IndoleHCID 9189PhenanthridineHCID 78284Cyclopentanecarbonyl chloride

Product 1

HCID 23118668HCID 23118668, compound

Procedure

Cyclopentyl-[6-(1H-indol-3-yl)-6H-phenanthridin-5-yl]-methanone was prepared from phenanthridine, cyclopentanecarboxylic acid chloride, and indole according to GP 2. Yield, 10%. 1H-NMR (DMSO-d6): δ=1.28-1.43 (m, 2H), 1.47-1.75 (m, 4H), 1.90-2.04 (m, 2H), 3.14-3.26 (m, 1H), 6.07 (s, br., 1H), 6.95-7.10 (m, 3H), 7.16 (td, J=7.6 Hz, J=1.6 Hz, 1H), 7.20-7.31 (m, 3H), 7.35-7.42 (m, 1H), 7.44-7.52 (m, 2H), 7.66 (d, J=7.4 Hz, 1H), 7.93 (d, J=7.4 Hz, 1H), 8.01 (d, J=7.5 Hz, 1H), 10.61 (s, 1H); (+)-ESI-MS: m/z=393 [M+H]+, 276 [M-indole+H]+, 180.

Workup

  1. customYield

Sources & evidence

ORD record
ord-786603c8b637443e9f9d051ce682b16e
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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