Sodium hydride → HCID 68181837, compound

Participants

Reaction Steps

To a solution of 2-(6-bromo-1H-indazol-3-yl)propan-2-ol (317 mg, 1.24 mmol) in DMF (10 mL) was added NaH (60% oil dispersion, 79.5 mg, 1.99 mmol) at 0° C. The reaction mixture was stirred at RT for 20 minutes before addition of 4-chloropyrimidin-2-amine (321.95 mg, 2.49 mmol). The mixture was stirred at RT for 10 minutes and then at 65° C. for 23 hr. The reaction mixture was quenched by addition of water (10 mL) and EtOAc (2 mL) was added. The resultant precipitate was collected by suction filtration and then thoroughly dried under high vacuum and triturated from diethyl ether. The crude product was purified by flash chromatography (Biotage, 1-5% methanol in DCM) to give the title intermediate as a pale yellow solid: 1H NMR (500 MHz, DMSO) delta 1.63 (6 H, s), 5.59 (1H, s), 7.23-6.93 (3H, m), 7.49 (1H, dd, J=8.6, 1.5 Hz), 8.07 (1H, d, J=8.6 Hz), 8.27 (1H, d, J=5.5 Hz), 9.11 (1H, d, J=1.4 Hz); LC-MS m/z=+347.95/349.80 (M+H)+.

Provenance & Evidence