3-Fluoro-5-(trifluoromethyl)benzoyl chloride → N-[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-fluoro-N-methyl-5-trifluoromethyl-benzamide

HRID 878135Notes

Reaction equation

HRID 878135 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[NH:15][CH3:16])=[C:4]([O:17][CH3:18])[CH:3]=1.[F:19][C:20]1[CH:21]=[C:22]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:23](Cl)=[O:24]>CCCCCCC.CCOC(C)=O>[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][C:10]=2[N:15]([CH3:16])[C:23](=[O:24])[C:22]2[CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=[C:20]([F:19])[CH:21]=2)=[C:4]([O:17][CH3:18])[CH:3]=1

Participants

4

Reactant 2

HCID 5193643-Fluoro-5-(trifluoromethyl)benzoyl chlorideHCID 70663277[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-methyl-amine

Product 1

HCID 86670751N-[4-(4,5-Difluoro-2-methoxy-phenyl)-pyridin-3-yl]-3-fluoro-N-methyl-5-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 72, intermediate, from [4-(4,5-difluoro-2-methoxy-phenyl)-pyridin-3-yl]-methyl-amine and 3-fluoro-5-(trifluoromethyl)benzoic acid chloride (CAS RN 171243-30-4) and using a gradient of n-heptane:EtOAc (100:0 to 20:80) for the chromatographic purification. Yellow solid (33%). MS (ESI): m/z=441.103 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-4d15b9342fa9412db0f8ee4e61e0e6ff
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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