8-Hydroxyquinoline → N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)-1H-indole-6-carboxamide

HRID 499792Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([CH2:13][NH:14][C:15]([C:17]3[CH:25]=[C:24]4[C:20]([CH:21]=[CH:22][NH:23]4)=[CH:19][CH:18]=3)=[O:16])[N:10]=[CH:9]2)=[CH:4][CH:3]=1.[OH:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I>[O:26]=[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]1[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([CH2:13][NH:14][C:15]([C:17]3[CH:25]=[C:24]4[C:20]([CH:21]=[CH:22][NH:23]4)=[CH:19][CH:18]=3)=[O:16])[N:10]=[CH:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)-1H-indole-6-carboxamide prepared above, 2-hydroxypyridine 1-7 (130 mg, 1.37 mmol), 8-hydroxyquinoline (30 mg, 0.21 mmol) and K2CO3 (246 mg, 1.78 mmol) in DMSO (2 mL) was degassed before being charged with CuI (43 mg, 0.23 mmol). The mixture in a sealed tube was heated at 130° C. overnight. It was then purified by HPLC to give the title compound (50 mg). MS 410.1 (M+H).

Workup

customwas degassed
customIt was then purified by HPLC

Sources & evidence

ORD record: ord-cb1808cef5934f92847d7c0007756e41
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767697B2

Reaction notes

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