4-(6-Methylimidazo[1,2-a]pyridin-2-yl)aniline → 3,4-difluoro-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamide

HRID 339568

Reaction equation

HRID 339568 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[F:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=1[F:28])[C:22](Cl)=[O:23]>N1C=CC=CC=1>[F:18][C:19]1[CH:20]=[C:21]([CH:25]=[CH:26][C:27]=1[F:28])[C:22]([NH:15][C:14]1[CH:16]=[CH:17][C:11]([C:9]2[N:10]=[C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]3[CH:8]=2)=[CH:12][CH:13]=1)=[O:23]

Participants

4

Reactant 2

HCID 8210844-(6-Methylimidazo[1,2-a]pyridin-2-yl)anilineHCID 27245193,4-Difluorobenzoyl chloride

Product 1

HCID 583419813,4-difluoro-N-[4-(6-methylimidazo[1,2-a]pyridin-2-yl)phenyl]benzamideYield 68.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Prepared as described in the Amide Coupling section using 4-(6-methylimidazo[1,2-a]pyridin-2-yl)aniline (0.50 g, 2.24 mmol) and 3,4-difluorobenzoyl chloride (0.395 g, 2.24 mmol) in dry pyridine (20 ml) to give the title compound (0.556 g, 68%) as a colourless solid after work-up and recrystallisation from AcOH.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-c21d0de92fd043f18b71606ca72dbfaf
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Linked notes

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