Dimethylformamide → 2-[4-(2-acetyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

Sodium hydride in mineral oil (3.65 g) was added to a solution of 5-(2-acetyl-phenoxy)-2H-pyridazin-3-one (16.3 g, 0.07 mol) in tetrahydrofuran (340 mL) at 0° C. The resulting mixture was stirred at 0° C. for 10 min and then was warmed to 20° C., where it stirred for 50 min. After this time, N,N-dimethylformamide (45 mL) and 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10, 25 g, 0.11 mol) were added to the reaction. The reaction was then warmed to 50° C. overnight. After this time, the reaction was concentrated in vacuo. Silica gel column chromatography afforded 2-[4-(2-acetyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-cyclopentyl-propionic acid methyl ester (23.4 g, 86%); ESI-MS 385 [M+H+].

Provenance & Evidence