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

Participants

Reaction Steps

To a solution of N-(1-{[4-chloro-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-2,6-difluorobenzamide (for a preparation see Example 80)(100 mg, 0.241 mmol) in a mixture of THF (0.9 ml) and N-methyl-2-pyrrolidone (0.1 ml) was added iron(III) acetylacetonate (17 mg, 0.048 mmol, Aldrich). The resulting red solution was stirred for 10 min and then treated with a solution of 15% isopropylmagnesium bromide in THF (1.2 ml, 0.60 mmol, Fluorochem) at ambient temperature. The solution was stirred at room temperature under nitrogen overnight. The reaction mixture was quenched with methanol (1 ml) and the solvent removed in vacuo. The residue was dissolved in 1:1 MeOH:DMSO (2 ml) and purified by MDAP (Method B) on Sunfire C18 column using Acetonitrile-Water with a Formic acid modifier. The solvent was evaporated in vacuo to give the title compound as a yellow solid (26 mg); LCMS: (System 4) MH+=424, tRET=3.41 min.

Provenance & Evidence