8-Hydroxyquinoline → 5-Chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-pyrazol-3-yl)methyl)thiophene-2-carboxamide

HRID 643038Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-pyrazol-3-yl)methyl)thiophene-2-carboxamide (60 mg, 0.14 mmol), 2-hydroxypyridine (30 mg, 0.32 mmol), 8-hydroxyquinoline (10 mg, 0.070 mmol) and K2CO3 (50 mg, 0.36 mmol) in DMSO (1 mL) was degassed with Argon before being charged with CuI (15 mg, 0.080 mmol). The mixture in a sealed tube was heated at 130° C. overnight. It was then purified by HPLC to give the titled compound (15 mg). MS 411.0 and 413.0 (M+H, Cl pattern).

Workup

customwas degassed with Argon
customIt was then purified by HPLC

Sources & evidence

ORD record: ord-8977820ed9ee4f868aca5b6b8d9919a3
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696352B2

Reaction notes

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