Indole → HCID 68488806, compound

HRID 1178719Notes

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.[C:15]1([CH3:24])[CH:20]=[CH:19][CH:18]=[C:17]([C:21](Cl)=[O:22])[CH:16]=1.[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26]1>>[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([CH:7]2[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]=3[N:6]2[C:21]([C:17]2[CH:16]=[C:15]([CH3:24])[CH:20]=[CH:19][CH:18]=2)=[O:22])=[CH:26]1

Participants

Reactant 3

HCID 798Indole

HCID 9189Phenanthridine

HCID 743753-Methylbenzoyl chloride

Product 1

HCID 68488806HCID 68488806, compound

Procedure

[6-(1H-Indol-3-yl)-6H-phenanthridin-5-yl]-m-tolyl-methanone was prepared from phenanthridine, m-toluoyl chloride, and indole according to GP 2. Yield, 13%. 1H-NMR (CD3CN): δ=2.22 (s, 3H), 6.22 (dd, J=2.5 Hz, J=1.0 Hz, 1H), 6.41 (s, br., 1H), 6.75 (t, J=7.5 Hz, 1H), 6.96 (d, J=7.5 Hz, 1H), 7.06-7.15 (m, 4H), 7.15-7.21 (m, 2H), 7.24-7.31 (m, 2H), 7.43 (ddd, J=J=7.3 Hz, J=1.2 Hz, 1H), 7.47-7.59 (m, 2H), 7.88 (dd, J=7.8 Hz, J=1.0 Hz, 1H), 7.93-8.00 (m, 1H), 8.04 (d, J=7.7 Hz, 1H), 8.90 (s, br., 1H); (+)-ESI-MS: m/z=415 [M+H]+, 298 [M-indole+H]+.

Workup

customYield

Sources & evidence

ORD record: ord-ed6809f6688d476f96858b0c441ee75c
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07276606B2

Reaction notes

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