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

HRID 643026Notes

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)[CH: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)[CH: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-pyrrol-3-yl)methyl)thiophene-2-carboxamide (118 mg, 0.27 mmol), 2-hydroxypyridine (50 mg, 0.53 mmol), 8-hydroxyquinoline (14 mg, 0.097 mmol) and K2CO3 (120 mg, 0.87 mmol) in DMSO (2 mL) was degassed with Argon before being charged with CuI (19 mg, 0.10 mmol). The mixture in a sealed tube was heated at 130° C. for 4 h. It was then purified by HPLC to give the titled compound (20 mg). MS 410.0 and 412.0 (M+H, Cl pattern).

Workup

customwas degassed with Argon
customIt was then purified by HPLC

Sources & evidence

ORD record: ord-5dbc56aa80f848dba2a388a30009b013
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696352B2

Reaction notes

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