Cesium carbonate → HCID 10759063, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(3-pyridyloxymethyl)-2-(trifluoromethanesulfonyloxy)benzoic acid methyl ester (216 mg, 0.55 mmol), prepared as in Example 203C, in 4 mL of DMF at 25° C. was added PdCl2(PPh3)2 (38 mg, 0.055 mmol, 10 mol %) followed by 2-tolyl boronic acid (113 mg, 0.83 mmol) and Cs2CO3 (270 mg, 0.83 mmol) and the reaction was heated to 80° C. for 12 hours. The reaction was then cooled to ambient temperature, taken up in 50 mL ethyl acetate, and washed with H2O (5×10 mL). The organic phase was dried over Na2SO4, filtered and evaporated to an oil. Purification by radial chromatography using a gradient of 25% ethyl acetate-hexanes to 75% ethyl acetate-hexanes gave 4-(3-pyridyloxymethyl)-2-(2-methylphenyl)benzoic acid methyl ester (178 mg, 97%) as an oil.

Provenance & Evidence