Sodium hydride → HCID 23362247, compound

Participants

Reaction Steps

A solution of trimethyl phosphonoacetate (5.5 mL) in dry tetrahydrofuran (25 mL) was added slowly to a cooled (cardice-acetone bath) suspension of sodium hydride (60% dispersion in oil, 1.34 g) in tetrahydrofuran (100 mL) under a nitrogen atmosphere such that the temperature of the reaction mixture remained between 0° C. and 10° C. during the addition. The resultant slurry was then cooled in an ice bath and stirred for 10 minutes prior to the addition of a solution of 4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzaldehyde (8.3 g) (Eur. Patent. Appl., Publication No. 0306228) in tetrahydrofuran (100 mL). The mixture was stirred at room temperature for 20 hrs, then quenched with brine (10 mL) and concentrated in vacuo. The residue was suspended in brine (500 mL) and extracted with dichloromethane (3×300 mL), and the combined organic layers washed with water (1 L) and brine (1 L), dried (MgSO4) and evaporated. The residue was chromatographed on silica gel with 1% methanol in dichloromethane as eluent to afford the title compound, mp 93°-5° C. (dichloromethane-hexane).

Provenance & Evidence