Sodium hydride → 4-{6-Bromo-3-[(morpholin-4-yl)carbonyl]indazol-1-yl}pyrimidin-2-amine

Participants

Reaction Steps

To a solution of 6-bromo-3-[(morpholin-4-yl)carbonyl]-1H-indazole (78%, 458 mg, 1.15 mmol) in DMF (8 mL) was added NaH (60% oil suspension, 73.71 mg, 1.84 mmol) at 0° C. Mixture was stirred at RT for 10 minutes before addition of 4-chloropyrimidin-2-amine (298.44 mg, 2.3 mmol). The mixture was stirred at RT for 10 minutes and then at 65° C. for 5 hr. Reaction mixture was quenched by addition of water (5 mL) and a little EtOAc (2 mL) was added. Precipitate formed was collected and dried under vacuum to give the title compound: 1H NMR (500 MHz, DMSO) delta 3.58-3.80 (6H, m), 3.87-4.13 (2H, m), 7.07 (1H, d, J=5.52 Hz), 7.59 (1H, dd, J=8.51, 1.42 Hz), 7.94 (1H, d, J=8.83 Hz), 8.35 (1H, d, J=5.52 Hz), 9.19 (1H, d, J=1.26 Hz); LC-MS: m/z=+404.8 (M+H)+.

Provenance & Evidence