Cesium carbonate → 2,6-difluoro-N-[1-({2-methyl-4-[(2-pyridinylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-yl]benzamide

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Reaction Steps

To a solution of 2,6-difluoro-N-{1-[(4-hydroxy-2-methylphenyl)methyl]-1H-pyrazol-3-yl}benzamide (for a preparation see Example 48)(103 mg, 0.30 mmol) in dimethyl sulfoxide (1 ml) was added cesium carbonate (195 mg, 0.60 mmol) and then 2-(bromomethyl)pyridine hydrobromide (107 mg, 0.423 mmol, Aldrich). The resulting red solution was stirred at ambient temperature under nitrogen overnight. The mixture was filtered using a hydrophobic frit and the filtrate diluted with methanol (1 ml). The filtrate was purified by MDAP on Sunfire C18 column using Acetonitrile-Water with a Formic acid modifier (Method B). The solvent was evaporated in vacuo to give the title compound as an orange gum (28.3 mg); LCMS: (System 4) MH+=435, tRET=2.27 min.

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