Ethyl Acetate → 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 (1.0 g, 4.5 mmol), dppf (0.25 g, 0.45 mmol), Pd2(dba3) (0.20 g, 0.22 mmol) and Zn(CN)2 (0.31 g, 2.7 mmol) in N-methylpyrrolidone (20 mL) was heated at 120° C. for 15 hours in a sealed vial. The residue was cooled to room temperature, treated with EtOAc (300 mL), washed with a solution of saturated aq. NH4Cl, conc. NOH, water (72 mL, a ratio of 4:1:4) and brine, dried over MgSO4, and concentrated. The crude was purified by silica gel flash column chromatography (100% CH2Cl2) to afford 0.77 g (80%) of the desired product. LRMS (ESI pos) m/e 216.0 (M+1). 1H-NMR (400 MHz, CDCl3) δ 7.58 (d, 1H), 7.46 (d, 1H), 7.42 (m, 2H), 7.26 (m, 2H); 19F-NMR (376 MHz, CDCl3) δ −109.6.

Provenance & Evidence