Indole → HCID 68485704, compound

HRID 1178737Notes

Reaction equation

HRID 1178737 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:19](Cl)=[O:20])[CH2:18][CH2:17][CH2:16]1.[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23]1>>[CH:15]1([C:19]([N:6]2[CH:7]([C:24]3[C:25]4[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=4)[NH:22][CH:23]=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:20])[CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 3

HCID 798IndoleHCID 9189PhenanthridineHCID 78705Cyclobutanecarbonyl chloride

Product 1

HCID 68485704HCID 68485704, compound

Procedure

Cyclobutyl-[6-(1H-indol-3-yl)-6H-phenanthridin-5-yl]-methanone was prepared from phenanthridine, cyclobutanecarboxylic acid chloride, and indole according to GP 2. Yield, 11%. 1H-NMR (DMSO-d6): δ=1.48-1.62 (m, 1H), 1.65-2.02 (m, 3H), 2.15-2.41 (m, 2H), 3.49-3.66 (m, 1H), 6.07 (s, br., 1H), 6.92-7.07 (m, 3H), 7.16 (t, J≈7.5 Hz, 1H), 7.19-7.30 (m, 3H), 7.35-7.42 (m, 1H), 7.43-7.52 (m, 2H), 7.68 (d, J=6.7 Hz, 1H), 7.92 (d, J=7.4 Hz, 1H), 8.01 (d, J=7.3 Hz, 1H), 10.62 (s, 1H); (+)-ESI-MS: m/z=379 [M+H]+, 262 [M-indole+H]+, 180.

Workup

  1. customYield

Sources & evidence

ORD record
ord-bc2d6913a8bb4ecbb1bb83209a387375
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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