Piperidine → HCID 60164409, compound

Participants

Reaction Conditions

Reaction Steps

To a pressure tube was added 4-(6-Bromo-5-fluoro-benzoimidazol-1-yl)-pyrimidin-2-ylamine (66%, 250 mg, 0.54 mmol), piperidine (1.5 mL), tetrakis(triphenylphosphine)palladium (61.9 mg, 0.05 mmol), copper(I) iodide (10.2 mg, 0.05 mmol) and 2-(1,3-thiazol-2-yl)but-3-yn-2-ol (164.09 mg, 1.07 mmol), degassed with N2 for 5 min and stirred at 75° C. for 3 hr before concentrating in vacuo. The crude product was purified by column chromatography (Biotage) eluted with DCM: methanol gradient (98:2 to 90:10). The product obtained was triturated with methanol to obtain the title compound as an off-white solid (35 mg, 17.1% yield). 1H NMR (500 MHz, DMSO) delta 1.94 (3H, s), 7.08 (1H, s), 7.13 (1H, d, J=5.36 Hz), 7.18 (2H, br. s.), 7.65-7.73 (2H, m), 7.78 (1H, d, J=3.15 Hz), 8.39 (1H, br. s.), 8.64 (1 H, d, J=6.46 Hz), 9.17 (1H, s); LC-MS: m/z+381.40 (M+H)+.

Provenance & Evidence