Piperidine → HCID 60164850, compound

Participants

Reaction Conditions

Reaction Steps

To a pressure tube was added 2-[1-(2-aminopyrimidin-4-yl)-6-bromoindazol-3-yl]propan-2-ol followed by piperidine (2.5 mL), tetrakis(triphenylphosphine)palladium (102.88 mg, 0.09 mmol), copper(I) iodide (16.96 mg, 0.09 mmol) and (2R)-2-(5-methyl-1,2-oxazol-3-yl)but-3-yn-2-ol (269.16 mg, 1.78 mmol). The reaction was capped and stirred at 65° C. for 1.5 hr and then concentrated in vacuo. DCM (5 mL) was added to the reaction mixture and the concentration was repeated (×2). The crude product was purified by flash chromatography (Biotage, 1-10% methanol in DCM) gave the title compound: 1H NMR (500 MHz, DMSO) delta 1.63 (6H, s), 1.85 (3H, s), 2.41 (3H, s), 5.57 (1H, s), 6.41 (1H, s), 6.56 (1H, s), 7.00 (2H, s), 7.05 (1H, d, J=5.5 Hz), 7.33 (1H, dd, J=8.3, 1.2 Hz), 8.13 (1H, d, J=8.3 Hz), 8.27 (1H, d, J=5.2 Hz), 8.88 (1H, s); LC-MS: m/z=+419.10 (M+H)+.

Provenance & Evidence