Indole → HCID 23118684, compound

HRID 1178731Notes

Reaction equation

HRID 1178731 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.[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20](Cl)=[O:21].[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24]1>>[O:15]1[CH:19]=[CH:18][CH:17]=[C:16]1[C:20]([N:6]1[CH:7]([C:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:23][CH:24]=2)[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2)=[O:21]

Participants

4

Reactant 3

HCID 798IndoleHCID 9189PhenanthridineHCID 682422-Furancarbonyl chloride

Product 1

HCID 23118684HCID 23118684, compound

Procedure

Furan-2-yl-[6-(1H-indol-3-yl)-6H-phenanthridin-5-yl]-methanone was prepared from phenanthridine, 2-furoyl chloride, and indole according to GP 2. Yield, 72%. 1H-NMR (DMSO-d6): δ=6.19 (“d”, J=2.1 Hz, 1H), 6.51 (dd, J=3.4 Hz, J=1.7 Hz, 1H), 6.61 (d, J=7.9 Hz, 1H), 6.71 (d, J=3.4 Hz, 1H), 6.95-7.08 (m, 3H), 7.17-7.27 (m, 2H), 7.41 (“t”, J≈7.5 Hz, 1H), 7.48-7.56 (m, 2H), 7.63-7.65 (m, 2H), 7.88 (d, J=7.0 Hz, 1H), 7.97 (d, J=7.9 Hz, 1H), 8.07 (d, J=7.8 Hz, 1H), 10.70 (s, 1H); (+)-ESI-MS: m/z=391 [M+H]+, 274 [M-indole+H]+.

Workup

  1. customYield

Sources & evidence

ORD record
ord-5ea8d64da1e84d1c80f9dc642f62d96b
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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