Triphenylphosphine → 3-[3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-ylmethoxy]-isoxazole-5-carboxylic acid methyl ester

Participants

Reaction Steps

To a solution of [3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-methanol (438 mg, 2.1 mmol) in THF (10 mL) was added 3-oxo-2,3-dihydro-isoxazole-5-carboxylic acid methyl ester (300 mg, 2.1 mmol) and triphenylphosphine (658 mg, 2.1 mmol) at room temperature under an argon atmosphere. Then diethyl azodicarboxylate (˜40% in toluene, 1.1 mL, 2.5 mmol) was added and the reaction mixture was stirred for 3 h at room temperature. Concentration and purification by chromatography (silica, dichloromethane:methanol=4:1 to 1:4) afforded the title compound (431 mg, 62%) as a white solid. MS: m/e=334.2 [M+H]+.

Provenance & Evidence