Sodium hydride → 6-[3-Butyl-5-([E]-styryl)-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester

Participants

Reaction Steps

To a suspension of sodium hydride (170 mg, 4.24 mmol) in THF (7 mL) at 0° C. was added a solution of [3-butyl-5([E]-styryl)-isoxazol-4-yl]-methanol (993 mg, 3.86 mmol) in THF (17 mL) and the mixture was stirred for 30 min at room temperature. The reaction mixture was cooled to 5° C. and a solution of methyl 6-bromonicotinate (1.0 g, 4.6 mmol) in THF (17 mL) was added dropwise. The mixture was stirred at room temperature for 2 days, poured over ice and stirred for 5 min. The mixture was extracted twice with ethyl acetate, washed with brine, dried over sodium sulfate and concentrated to a yellow oily solid. The crude material was purified by flash chromatography (silica gel, heptane:ethyl acetate 1:0 to 3:2) to afford the title compound (1.17 g, 77%) as an orange semisolid. MS: m/e=393.2 [M+H]+.

Provenance & Evidence