Sodium hydride → 2-[(2-chloro-5-cyanopyridin-4-yl)amino]-N-methoxy-N-methylbenzamide

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Reaction Conditions

Reaction Steps

Sodium hydride (0.888 g, 22.20 mmol) was added portionwise to a mixture of 2-amino-N-methoxy-N-methylbenzamide (1.00 g, 5.55 mmol), in THF (30 mL) cooled to 0° C. under an atmosphere of nitrogen. The resulting suspension was stirred at room temperature for 20 minutes and then 4,6-dichloropyridine-3-carbonitrile (0.960 g, 5.55 mmol) was added portionwise and the mixture heated overnight at 60° C. The mixture was allowed to cool to room temperature and then diluted with EtOAc (50 mL). The mixture was washed sequentially with water (50 mL), a saturated solution of NaHCO3 (50 mL), water (25 mL) and finally with a saturated solution of NaCl (20 mL). The organic layer was dried over Na2SO4 and then evaporated. The residue was crystallised from Et2O/MeOH to afford 2-[(2-chloro-5-cyanopyridin-4-yl)amino]-N-methoxy-N-methylbenzamide (0.602 g, 34% yield); 1H NMR spectrum: (300 MHz, DMSO) δ 3.15 (3H, s), 3.47 (3H, s), 6.56 (1H, s), 7.39-7.44 (2H, m), 7.52-7.56 (2H, m), 8.45 (1H, s), 9.33 (1H, s); Mass spectrum: m/z (ESI+) (M+H)+=317.28 and 319.30.

Provenance & Evidence