Sodium hydride → HCID 86646258, compound

Participants

Reaction Steps

To a suspension of sodium hydride (129 mg, 3.22 mmol) in THF (4.5 mL) was added a solution of (E)-(3-(5-fluoropyridin-2-yl)-5-styrylisoxazol-4-yl)methanol (866 mg, 2.92 mmol) in THF (9 mL) at room temperature. The reaction mixture was stirred for 1 h at room temperature. A solution of methyl 6-chloronicotinate (602 mg, 3.51 mmol) in THF (9 mL) was added. The reaction was stirred at room temperature overnight and water (150 mL) and saturated aqueous ammonium chloride solution (100 mL) were added. Extraction with ethyl acetate and chromatography (silica, ethyl acetate:heptane=1:9 to 2:3) afforded the title compound (906 mg, 66%) as a white solid. MS: m/e=432.2 [M+H]+.

Provenance & Evidence