Piperidine → 1-(2-aminopyrimidin-4-yl)-N,N-dimethyl-6-[2(trimethylsily)ethynyl]indazole-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1-(2-aminopyrimidin-4-yl)-6-bromo-N,N-dimethylindazole-3-carboxamide (61-b) (500 mg, 1.27 mmol), tetrakis(triphenylphosphine)palladium (118 mg, 0.102 mmol), copper(I) iodide (19.4 mg, 0.102 mmol) and ethynyl(trimethyl)silane 0.39 ml, 2.54 mmol) was added piperidine (3.1 mL). The mixture was purged with nitrogen for 2 minutes and then stirred at 65° C. for 4 hr. The reaction mixture was concentrated in vacuo, DCM (5 mL) was added and the concentration repeated (×2). The crude product was purified by flash chromatography (Biotage, 2-8% methanol in DCM) to give the title intermediate (250 mg): LC-MS: m/z=+379.45 (M+H)+.

Provenance & Evidence