Sodium Carbonate → 6-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-6-chloro-pyridazine and 3-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-6-iodo-pyridazine (˜1:3 mixture, 2.6 g, ˜7.0 mmol) and sodium carbonate (738 mg, 7.0 mmol) in methanol (20 mL) was evacuated and filled with argon five times. 1,1′-Bis(diphenylphosphino)ferrocene (386 mg, 0.7 mmol) and palladium(II) acetate (156 mg, 0.7 mmol) were added then the flask was evacuated again and filled with carbon monoxide. The reaction mixture was then heated to 50° C. After 15 h the reaction mixture was cooled, filtered through decalite and evaporated. The residue was purified by chromatography (silica, 0 to 50% ethyl acetate in heptane) to give the title compound (760 mg, ˜36%) as an orange solid. MS: m/e=306.1 [M+H]+.

Provenance & Evidence