Dimethylformamide → 6-Amino-5-methoxy-nicotinonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-3-methoxy-pyridin-2-amine (3.00 g, 14.8 mmol) in N,N-dimethylformamide (55 mL) under a nitrogen atmosphere was added zinc (II) cyanide (2.78 g, 23.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (2.06 g, 1.77 mmol). The reaction mixture was stirred at 100° C. for 4 h. The reaction mixture was diluted with ethyl acetate and washed successively with a saturated solution of ammonium hydroxide and brine. The phases were separated. The organic phases was dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:5) to give 6-amino-5-methoxy-pyridine-3-carbonitrile (1.2 g, 54% yield). 1H NMR (400 MHz, CDCl3): 7.99 (s, 1H), 6.99 (s, 1H), 3.88 (s, 3H) ppm. 13C NMR (100 MHz, CDCl3): 152.83, 144.58, 141.27, 118.32, 115.52, 97.66, 55.65. LC-MS (Method B): RT 0.69, 150 (M+H+)

Provenance & Evidence