3-Chloro-2-fluorophenylboronic Acid → N-[4-(3-Chloro-2-fluoro-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

HRID 878107Notes

Reaction equation

HRID 878107 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]([CH3:25])[C:9](=[O:24])[C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1.[Cl:26][C:27]1[C:28]([F:36])=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=1>CCCCCCC.CCOC(C)=O>[Cl:26][C:27]1[C:28]([F:36])=[C:29]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N:8]([CH3:25])[C:9](=[O:24])[C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)[CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 2

HCID 162171583-Chloro-2-fluorophenylboronic AcidHCID 86670697N-(4-iodopyridin-3-yl)-N-methyl-3,5-bis(trifluoromethyl)benzamide

Product 1

HCID 86670733N-[4-(3-Chloro-2-fluoro-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 72, from N-(4-iodo-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide (example 98, intermediate a) and 3-chloro-2-fluorophenylboronic acid (CAS RN 352535-82-1) and using a gradient of n-heptane:EtOAc (100:0 to 30:70) for the chromatographic purification. Light yellow oil (64%). MS (ESI): m/z=477.061 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-aa4206789e3a4c22976e8556c84da4c7
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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