2-(Pyridin-2-yl)but-3-yn-2-ol → 4-[1-(2-aminopyrimidin-4-yl)-3-(2-hydroxypropan-2-yl)-1H-indazol-6-yl]-2-(pyridin-2-yl)but-3-yn-2-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[1-(2-aminopyrimidin-4-yl)-6-iodo-1H-indazol-3-yl]propan-2-ol (150 mg, 0.36 mmol) in piperidine (2 mL) was introduced tetrakis(triphenylphosphine)palladium (0) (16.8 mg, 0.02 mmol), copper(I) iodide (2.8 mg, 0.02 mmol) and 2-(pyridin-2-yl)but-3-yn-2-ol (112 mg, 0.73 mmol). The reaction was warmed to 35° C. for 1 hr. After cooling to RT, the reaction mixture was concentrated in vacuo and the residue purified by flash chromatography (Biotage, DCM containing a 1-10% MeOH gradient) to furnish the title compound as a brown oil: 1H NMR (500 MHz, CDCl3) delta 1.78 (6H, s), 1.94 (3H, s), 2.84 (1H, br. s.), 5.18 (2H, br. s.), 5.80 (1H, br. s.), 7.19-7.39 (1H, m), 7.74 (1H, d, J=7.88 Hz), 7.82 (1H, td, J=7.72, 1.58 Hz), 7.90 (1H, d, J=8.35 Hz), 8.29 (1H, d, J=5.36 Hz), 8.58 (1H, d, J=4.73 Hz), 8.89 (1 H, s); LCMS: m/z=+415.05 (M+H)+.

Provenance & Evidence