2,3-Dimethylphenylboronic acid → N-[4-(2,3-Dimethyl-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

HRID 878100Notes

Reaction equation

HRID 878100 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.[CH3:26][C:27]1[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O>CCCCCCC.CCOC(C)=O>[CH3:26][C:27]1[C:32]([CH3:33])=[CH:31][CH:30]=[CH:29][C:28]=1[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

Participants

4

Reactant 2

HCID 27733952,3-Dimethylphenylboronic acidHCID 86670697N-(4-iodopyridin-3-yl)-N-methyl-3,5-bis(trifluoromethyl)benzamide

Product 1

HCID 86670727N-[4-(2,3-Dimethyl-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 2,3-dimethylphenylboronic acid (CAS RN 183158-34-1) and using gradient of n-heptane:EtOAc (100:0 to 30:70) for the chromatographic purification. Colorless solid (81%). MS (ESI): m/z=453.140 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-bbacee8cc041429392bf0145586183cf
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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