Sodium hydride → HCID 66875397, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 5-phenoxy-2H-pyridazin-3-one (1.42 g, 7.54 mmol) in tetrahydrofuran (37.7 mL, 0.2M) cooled to 0° C. was treated with a 60% suspension of sodium hydride in mineral oil (362 mg, 9.05 mmol). The reaction stirred at 0° C. for 5 min and then at 25° C. for an additional 30 min. After this time, the reaction was treated with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10, 1.95 g, 8.30 mmol). The reaction was then warmed to 50° C., where it stirred for 18 h. After this time, the reaction was partitioned between water (300 mL) and methylene chloride (3×100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. Silica gel column chromatography (Isco 40 g, 20% ethyl acetate/hexanes) afforded 3-cyclopentyl-2-(6-oxo-4-phenoxy-6H-pyridazin-1-yl)-propionic acid methyl ester (1.72 g, 66%) as a clear oil; ES+-HRMS m/e calcd for C19H22N2O4 [M+H+] 343.1653, found 343.1652.

Provenance & Evidence