Isopropylamine → 5-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid isopropylamide

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Reaction Steps

To a stirred solution of isopropylamine (98 mg, 1.66 mmol) in dioxane (3 mL) was added dropwise a trimethylaluminium (0.83 mL, 2 M solution in toluene, 1.66 mmol) and the resulting solution stirred under argon for 30 min. A solution of 5-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine-2-carboxylic acid ethyl ester (140 mg, 0.41 mmol) in dioxane (3 mL) was then added and the resulting solution stirred under argon for a further 20 h at 85° C. The reaction mixture was cooled and Seignette salt solution (2 mL) and water (2 mL) were added. The reaction mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were dried, filtered and concentrated in vacuo. Purification by chromatography (silica, 0 to 6% methanol in dichloromethane) gave the title compound (138 mg, 95%) as a light yellow solid. MS: m/e=352.3 [M+H]+.

Provenance & Evidence