Indole → HCID 68488737, compound

HRID 1178716Notes

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.[F:15][C:16]([F:27])([F:26])[C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1.[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29]1>>[NH:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([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:20]2[CH:24]=[CH:25][C:17]([C:16]([F:27])([F:26])[F:15])=[CH:18][CH:19]=2)=[O:22])=[CH:29]1

Participants

Reactant 3

HCID 798Indole

HCID 9189Phenanthridine

HCID 676074-(Trifluoromethyl)benzoyl chloride

Product 1

HCID 68488737HCID 68488737, compound

Procedure

[6-(1H-Indol-3-yl)-6H-phenanthridin-5-yl]-(4-trifluoromethyl-phenyl)-methanone was prepared from phenanthridine, 4-trifluoromethylbenzoyl chloride, and indole according to GP 2. Yield, 12%. 1H-NMR (CD3OD): δ=6.19 (s, 1H), 6.28 (s, br., 1H), 6.75 (t, br., J≈6.8 Hz, 1H), 7.03-7.11 (m, 2H), 7.14 (t, J=7.6 Hz, 1H), 7.20-7.25 (m, 1H), 7.33-7.51 (m, 5H), 7.52-7.60 (m, 1H), 7.57 (d, J=7.6 Hz, 2H), 7.92 (d, J=7.8 Hz, 1H), 7.99 (s, br., 1H), 8.07 (d, J=7.8 Hz, 1H); (+)-ESI-MS: m/z=469 [M+H]+, 352 [M-indole+H]+.

Workup

customYield

Sources & evidence

ORD record: ord-0243c7fb9e0b4431bf85f81238125894
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07276606B2

Reaction notes

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