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

HRID 643038
Notes
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Reaction equation

HRID 643038 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 11430Potassium CarbonateHCID 685066795-chloro-N-((1-(4-iodophenyl)-1H-pyrazol-3-yl)methyl)thiophene-2-carboxamideHCID 178516071HCID 178516071, compound

Product 1

HCID 592601105-Chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-pyrazol-3-yl)methyl)thiophene-2-carboxamideYield 26.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

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

  1. customwas degassed with Argon
  2. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes