Sodium hydride → 4-(6-Bromo-5-fluoro-3-methylindazol-1-yl)pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-bromo-5-fluoro-3-methyl-1H-indazole (130 mg, 0.284 mmol, 50% purity) in DMF (2 ml) was added NaH (60% oil dispersion, 18.16 mg, 0.454 mmol) at 0° C. The reaction mixture stirred for 15 minutes before the slow addition of a solution of 4-chloropyrimidin-2-amine (73.53 mg, 0.568 mmol) in DMF (2 mL). The resulting mixture was stirred at 60° C. for 16 hr. The reaction mixture was cooled and partitioned between water (15 ml) and EtOAc (15 ml). A precipitate formed and was collected by suction filtration. The filtrate was concentrated in vacuo and purified by flash chromatography (Isolute column, 1-2% methanol in DCM) to give the title intermediate as a yellow oil: 1H NMR (500 MHz, DMSO) delta 2.56 (3H, s), 7.00 (1H, s), 7.04-7.14 (2H, m), 7.92 (1H, d, J=8.35 Hz), 8.26 (1H, d, J=5.52 Hz), 9.22 (1H, d, J=5.99 Hz); LC-MS: m/z=+321.90, 323.80 (M+H)+.

Provenance & Evidence