Piperidine → 4-[1-(2-aminopyrimidin-4-yl)-3-[(morpholin-4-yl)carbonyl]-1H-indazol-6-yl]-2-(1,3-oxazol-2-yl)but-3-yn-2-ol

Participants

Reaction Conditions

Reaction Steps

To a pressure tube was added 4-{6-iodo-3-[(morpholin-4-yl)carbonyl]-1H-indazol-1-yl}pyrimidin-2-amine (150 mg, 0.33 mmol) followed by piperidine (2.0 mL), tetrakis(triphenylphosphine)palladium(0) (38.5 mg, 0.03 mmol), copper(I) iodide (6.35 mg, 0.03 mmol) and 2-(1,3-oxazol-2-yl)but-3-yn-2-ol (68.53 mg, 0.5 mmol). The reaction was capped and stirred at 35° C. for 2.5 hr. The reaction mixture was concentrated in vacuo. DCM (5 mL×2) added and the mixture was concentrated in vacuo. Purification by column chromatography (1% to 10% MeOH in DCM), followed by trituration with a mixture of MeCN/diethyl ether mixture (3/1) gave the title compound as an off-white solid (62 mg): 1H NMR (500 MHz, DMSO) delta 3.67 (2H, d, J=4.26 Hz), 3.75 (4H, d, J=5.67 Hz), 3.94 (2H, d, J=3.94 Hz), 4.06 (3H, s), 6.72-6.89 (1H, m), 6.93-7.33 (4H, m), 7.45 (1H, d, J=7.57 Hz), 8.04 (1H, d, J=7.88 Hz), 8.11-8.23 (1H, m), 8.97 (1H, s); LC-MS: m/z=+460.15 (M+H)+.

Provenance & Evidence