Isopropenyl chloroformate → HCID 89815666, compound

Participants

Reaction Steps

Treat a 0° C. solution of 3-(5-amino-2,4-difluorophenyl)-N,2-dimethyl-1,6-naphthyridin-7-amine (1.45 g, 4.83 mmol) in pyridine (30 mL) drop-wise with isopropenyl chloroformate (0.528 mL, 4.83 mmol), warm to RT and stir overnight. Add EtOAc, wash with satd. NaHCO3 (2×), dry, concentrate and purify by silica gel chromatography (EtOAc/TEA pre-wash, EtOAc/Hex) to afford the title compound (1.449 g, 78%). 1H NMR (400 MHz, DMSO-d6): δ 9.77 (s, 1H), 8.85 (s, 1H), 8.03 (s, 1H), 7.67-7.63 (m, 1H), 7.49 (t, 1H), 6.87-6.84 (m, 1H), 6.52 (s, 1H), 4.73 (s, 1H), 4.70 (s, 1H), 2.82 (d, 3H), 2.38 (s, 3H), 1.91 (s, 3H); MS (ESI) m/z: 385.2 (M+H+).

Provenance & Evidence