Indole → 1-[6-(1H-indol-3-yl)-6H-phenanthridin-5-yl]ethanone

HRID 1178712Notes

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](Cl)(=[O:17])[CH3:16].[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20]1>>[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([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:15](=[O:17])[CH3:16])=[CH:20]1

Participants

Reactant 3

HCID 798Indole

HCID 6367Acetyl chloride

HCID 9189Phenanthridine

Product 1

HCID 116529811-[6-(1H-indol-3-yl)-6H-phenanthridin-5-yl]ethanone

Procedure

1-[6-(1H-Indol-3-yl)-6H-phenanthridin-5-yl]-ethanone was prepared from phenanthridine, acetyl chloride, and indole according to GP 2. Yield, 30%. 1H-NMR (CDCl3): δ=2.25 (s, 3H), 6.16 (d, J=1.6 Hz, 1H), 7.10 (td, J=7.7 Hz, J=1.1 Hz, 1H), 7.12-7.17 (m, 2H), 7.18-7.25 (m, 2H), 7.31-7.48 (m, 3H), 7.50 (s, 1H), 7.73 (s, br., 1H), 7.81 (d, J=7.8 Hz, 1H), 7.89 (d, J=7.8 Hz, 1H), 7.93-8.00 (m, 1H); (+)-ESI-MS: m/z=339 [M+H]+, 222 [M-indole+H]+.

Workup

customYield

Sources & evidence

ORD record: ord-64b01f38189e471b899f3d021497a34e
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07276606B2

Reaction notes

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