Water → HCID 178522844, compound

Participants

Reaction Conditions

Reaction Steps

N-(4-Cyanomethyl-2-fluoro-benzyl )-2-(4-fluoro-phenoxy)-nicotinamide (0.100 g) was combined with sodium azide (0.653 g) and triethylamine hydrochloride (0.334 g) in anhydrous toluene (4 mL). The reaction mixture was heated under nitrogen in a sealable tube in an oil bath (116° C.) overnight. The reaction mixture was then allowed to cool to ambient temperature. Water (10 mL) and ethyl acetate (10 mL) were added, and the organic layer was separated. The pH of the aqueous layer was adjusted to 3 with 3N hydrochloric acid. The aqueous layer was subsequently extracted with ethyl acetate (5×15 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography (acetic acid:methanol:dichloromethane=1:5:94) to yield the title compound (0.33 g).

Provenance & Evidence