Potassium Phosphate, Tribasic → 5-Cyclopropyl-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl ester

Participants

Reaction Steps

Under an atmosphere of nitrogen, a solution of 5-bromo-6-(2-methoxyethoxy)-pyridine-2-carboxylic acid methyl ester (0.2 g, 0.7 mmol), cyclopropylboronic acid (CAN 411235-57-9, 81 mg, 0.9 mmol), palladium acetate (CAN 3375-31-3, 8 mg, 0.037 mmol), tricyclohexylphosphine (CAN 2622-14-2, 0.021 g, 0.07 mmol) and potassium phosphate (0.54 g, 0.20 mmol) in toluene (20 mL) and water (1 mL) was heated to 110° C. for 48 h. The reaction mixture was concentrated under reduced pressure, dissolved in water, extracted with ethyl acetate (3×30 mL), washed with brine, dried (sodium sulfate) and evaporated to dryness. The residue was purified by column chromatography (silica gel, 10 g, 5% ethyl acetate in petroleum ether) to yield the title compound (0.16 g, 1 mmol, 93%) as yellow oil; MS (EI): m/e 252.2 [M+H]+.

Provenance & Evidence