Pyrrole → HCID 23118675, compound

HRID 1178745Notes

Reaction equation

HRID 1178745 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[CH:27]=[CH:26][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:24]2[NH:23][CH:27]=[CH:26][CH:25]=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 8027PyrroleHCID 9189PhenanthridineHCID 682422-Furancarbonyl chloride

Product 1

HCID 23118675HCID 23118675, compound

Procedure

Furan-2-yl-[6-(1H-pyrrol-2-yl)-6H-phenanthridin-5-yl]-methanone was prepared from phenanthridine, 2-furoyl chloride, and pyrrole according to GP 2. Yield, 25%. 1H-NMR (DMSO-d6): δ=5.16 (s, 1H), 5.68 (q, J=2.7 Hz, 1H), 6.52-6.59 (m, 2H), 6.74 (s, 1H), 6.78 (d, J=3.3 Hz, 1H), 6.91 (d, J=7.8 Hz, 1H), 7.11 (td, J=7.7 Hz, J=1.1 Hz, 1H), 7.22 (td, J=7.5 Hz, J=1.2 Hz, 1H), 7.39 (td, J=7.4 Hz, J=0.9 Hz, 1H), 7.44-7.54 (m, 2H), 7.68 (s, 1H), 7.91 (dd, J=7.9 Hz, J=1.1 Hz, 1H), 8.00 (d, J=7.6 Hz, 1H), 10.61 (s, 1H); (+)-ESI-MS: m/z=274 [M-pyrrole]+.

Workup

  1. customYield

Sources & evidence

ORD record
ord-0886f9ead01842e8be7dd85336fb420b
Source dataset
uspto-grants-2007_10
Patent number
US07276606B2

Reaction notes

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