2,6-Difluoro-N-(1-{[4-iodo-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)benzamide → 2,6-Difluoro-N-(1-{[4-(2-methylpropyl)-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,6-difluoro-N-(1-{[4-iodo-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)benzamide (for a preparation see Example 73)(75 mg, 0.148 mmol) in THF (1 ml) was added tetrakis(triphenyl-phosphine)palladium (0) (17.1 mg, 0.015 mmol, Aldrich). To the solution was added 0.5 M t-butylzinc bromide in THF (0.6 ml, 0.30 mmol, Aldrich) and the mixture stirred at 80° C. under nitrogen for 3 h. A further amount of tetrakis (triphenylphosphine) palladium (0) (30 mg) and then 0.5 M t-butylzinc bromide in THF (1 ml, 0.5 mmol) was added to the mixture at ambient temperature. The mixture was heated to 80° C. for a further 3 h. The solvent was removed in vacuo and the residue dissolved in 1:1 MeOH:DMSO ml×2 and purified by MDAP on Sunfire C18 column (Method B) using Acetonitrile-Water with a Formic acid modifier. The solvent was evaporated in vacuo to give the title compound as a brown gum (12 mg); LCMS: (System 4) MH+=438, tRET=3.47 min.

Provenance & Evidence