4-(6-Methylimidazo[1,2-a]pyridin-2-yl)aniline → HCID 58342020, compound

HRID 339573Notes

Reaction equation

HRID 339573 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.[CH3:18][O:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][C:21]=1[C:29]([F:32])([F:31])[F:30].CCOC(C)=O.CCCCCC>N1C=CC=CC=1>[CH3:18][O:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:15][C:14]2[CH:16]=[CH:17][C:11]([C:9]3[N:10]=[C:5]4[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]4[CH:8]=3)=[CH:12][CH:13]=2)=[O:25])=[CH:22][C:21]=1[C:29]([F:30])([F:31])[F:32]

Participants

5

Reactant 3

HCID 8210844-(6-Methylimidazo[1,2-a]pyridin-2-yl)anilineHCID 27752984-Methoxy-3-(trifluoromethyl)benzoyl chlorideHCID 21226206Ethyl acetate hexane

Product 1

HCID 58342020HCID 58342020, compoundYield 38.5%

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 (0.20 g, 0.897 mmol) and 4-methoxy-3-trifluoromethylbenzoyl chloride (0.21 g, 0.897 mmol) in dry pyridine (15 ml) to give the title compound as a colourless solid (0.147 g, 38%) after work-up and flash chromatography (15:1 EtOAc/Hexane).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-ab14ba6b8cf7402ab8aa7f67062beae0
Source dataset
uspto-grants-2014_11
Patent number
US08895313B2

Reaction notes

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