3-chloro-1-(4-fluorophenyl)pyrazin-2(1H)-one → 4-(4-Fluorophenyl)-3-oxo-3,4-dihydropyrazine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-chloro-1-(4-fluorophenyl)pyrazin-2(1H)-one (3.52 g, 15.7 mmol), CuCN (2.81 g, 31.3 mmol) and N-methylpyrrolidone (30 mL) was heated for 5.5 hours at 150° C. while being stirred. The residue was triturated with hot CHCl3 and filtered over charcoal. The filtrate was evaporated and concentrated under reduced pressure. The residue was triturated with CH2Cl2 and the solution was concentrated. The crude was purified by silica gel flash column chromatography (3:1=CH2Cl2:Hexane then CH2Cl2) to afford 0.78 g (23%) of the desired product. LRMS (ESI pos) m/e 215.9 (M+1).

Provenance & Evidence