Sodium Bicarbonate → 2,6-Difluoro-N-(1-{[2-methyl-6-(methyloxy)phenyl]methyl}-1H-pyrazol-3-yl)benzamide

Participants

Reaction Steps

To a stirred solution of 2,6-difluoro-N-1H-pyrazol-3-ylbenzamide (for a preparation see Intermediate 9)(50 mg, 0.224 mmol) in dry THF (1.75 ml) under nitrogen was added 1.0 lithium bis(trimethylsilyl)amide in THF (0.2 ml, 0.2 mmol) dropwise and the solution stirred for 30 min. To the solution was added a solution of 2-(bromomethyl)-1-methyl-3-(methyloxy)benzene (for a preparation see intermediate 57)(48 mg, 0.224 mmol) in THF (1.75 ml). The solution was stirred for 1.5 h and then allowed to stand overnight. The solvent was blown down using a stream of nitrogen and aqueous sodium bicarbonate added to the residue. The aqueous phase was then extracted with chloroform. The organic extract was removed in vacuo to give a gum (84 mg). The residue was purified on MDAP (Method B). The solvent was removed and the residue dried at −45° C. under high vacuum to give the title compound as a white solid; LCMS (System 4) MH+=358, tRET=2.77 min.

Provenance & Evidence