Dichloromethane → Methyl 3-ethynyl-5-(5-methylpyridin-2-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of methyl 3-bromo-5-(5-methylpyridin-2-yl)benzoate (200 mg, 0.653 mmol) in dioxane (3 mL) was added tributyl(ethynyl)tin (247 mg, 0.784 mmol), cesium fluoride (198 mg, 1.31 mmol) and bis(tri-t-butylphosphine) palladium (16.7 mg, 0.033 mmol) and the mixture heated to 70° C. After 2 h, the reaction was cooled to ambient temperature and dichloromethane (50 mL was added). The organic layer was washed with 30 mL of saturated aqueous sodium bicarbonate (2×), dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) to give the title compound (145 mg). MS 252.1 (M+1).

Provenance & Evidence