869557-28-8

557-21-1

26163-03-1

869557-28-8

2-Amino-3-bromo-5-chloropyridine (2700.0 mg, 13.00 mmol) was dissolved in N-methylpyrrolidone (NMP, 60.0 mL), followed by the addition of zinc cyanide (Zn(CN)2, 2300.0 mg, 19.50 mmol) and tetrakis(triphenylphosphine)palladium (Pd(PPh3)4, 1500.0 mg, 1.30 mmol). The reaction mixture was stirred at 110 °C for 5 hours and then cooled to room temperature. Water and ethyl acetate (EtOAc) were added to the reaction mixture, stirred for 10 minutes and then filtered through diatomaceous earth. The filtrate was extracted with ethyl acetate, the organic layer was washed with brine, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent ratio: ethyl acetate/hexane = 1:9). The fraction containing the target product was collected and the solvent was evaporated to give 2-amino-5-chloronicotinonitrile as a white solid (1900.0 mg, 100% yield).LCMS ESI (+): m/z 154 ([M+H]+), 156 ([M+H+2]+).1H-NMR (300 MHz, DMSO-d6) δ: 8.22 (d, 1H, J = 2.7 Hz), 8.07 (d, 1H, J = 2.7 Hz), 7.14 (s, 2H).