Isopropylamine → HCID 49804754, compound

Participants

Reaction Conditions

Reaction Steps

Trimethylaluminium (1.22 mL of a 2 M solution in toluene, 2.44 mmol) was added dropwise to a stirred solution of isopropylamine (144 mg, 2.46 mmol) in dioxane (4 mL) at room temperature and under argon. After 1 h, a solution of 6-[5-methyl-3-(3,3,3-trifluoro-propyl)-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (210 mg, 0.61 mmol) in dioxane (4 mL) was added and the reaction mixture warmed to 90° C. After 10 h the reaction mixture was cooled and poured onto ice/water. The resultant mixture was extracted with ethylacetate then the combined extracts were washed with Seignette salt solution. The organic phase was dried, filtered and evaporated then purified by chromatography (silica, 0 to 60% ethyl acetate in heptane) then trituration with diisopropyl ether to give the title compound (145 mg, 64%) as a white solid. MS: m/e=372.3 [M+H]+.

Provenance & Evidence