Isopropylamine → 6-[3-(3,4-Difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-N-isopropyl-nicotinamide

Participants

Reaction Conditions

Reaction Steps

A trimethylaluminium solution (2M in toluene, 798 ul, 1.60 mmol) was added to a solution of isopropylamine (63.2 mg, 1.06 mmol) in dioxane (5 mL). 6-[3-(3,4-Difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (100 mg, 0.27 mmol) in dioxane (5 mL) was added after 1 h at 50° C. The reaction mixture was stirred at 85° C. overnight. The solvent was removed by distillation. The residue was purified by chromatography (silica, ethyl acetate:heptane=2:3 to 7:3) to afford the title compound (30 mg, 28%) as a light brown solid. MS: m/e=404.3 [M+H]+.

Provenance & Evidence