Pyrrole → HCID 86602189, compound

HRID 1178746Notes

Reaction equation

HRID 1178746 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:31])([F:30])[C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[C:20](Cl)=[O:21].[NH:32]1[CH:36]=[CH:35][CH:34]=[CH:33]1>>[F:15][C:16]([F:31])([F:30])[C:17]1[CH:18]=[C:19]([C:20]([N:6]2[CH:7]([C:33]3[NH:32][CH:36]=[CH:35][CH:34]=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:21])[CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1

Participants

4

Reactant 3

HCID 8027PyrroleHCID 9189PhenanthridineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chloride

Product 1

HCID 86602189HCID 86602189, compound

Procedure

(3,5-Bis-trifluoromethyl-phenyl)-[6-(1H-pyrrol-2-yl)-6H-phenanthridin-5-yl]-methanone was prepared from phenanthridine, 3,5-bis(trifluoromethyl)benzoyl chloride, and pyrrole according to GP 2. Yield, 12.5%. 1H-NMR (DMSO-d6): δ=5.21 (s, 1H), 5.79 (q, J=2.8 Hz, 1H), 6.59-6.63 (m, 1H), 6.64 (s, br., 1H), 6.84-7.09 (m, br., 2H), 7.21 (t, J=7.5 Hz, 1H), 7.43 (t, J=7.3 Hz, 1H), 7.51 (t, J≈7 Hz, 1H), 7.57 (d, J=7.1 Hz, 1H), 7.86 (s, br., 2H), 7.96 (d, J=7.8 Hz, 1H), 8.08 (d, J=7.5 Hz, 1H), 8.19 (s, 1H), 10.66 (s, 1H); (+)-ESI-MS: m/z=420 [M-pyrrole]+.

Workup

  1. customYield

Sources & evidence

ORD record
ord-bf210b69518f4821a21f79da13d24e95
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

Loading…