2-[1-(2-amino-5-chloropyrimidin-4-yl)-6-iodo-1H-indazol-3-yl]propan-2-ol → (2R)-4-[1-(2-amino-5-chloropyrimidin-4-yl)-3-(2-hydroxypropan-2-yl)-1H-indazol-6-yl]-2-(5-meth yl-1,2,4-oxadiazol-3-yl)but-3-yn-2-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[1-(2-amino-5-chloropyrimidin-4-yl)-6-iodo-1H-indazol-3-yl]propan-2-ol (150 mg, 0.35 mmol) in piperidine (2 mL) was introduced tetrakis(triphenylphosphine)palladium (0) (40.3 mg, 0.02 mmol), copper(I) iodide (6.6 mg, 0.02 mmol) and (2R)-2-(5-methyl-1,2,4-oxadiazol-3-yl)but-3-yn-2-ol (106 mg, 0.70 mmol). The reaction was warmed to 35° C. for 1.5 hr. After cooling to RT, the reaction mixture was concentrated in vacuo and the residue purified by silica gel flash column chromatography (heptane/EtOAc gradient) to furnish the title compound as a dark red solid: 1H NMR (500 MHz, DMSO-d6) delta 1.69 (6H, s), 1.93 (3H, s), 2.69 (3H, s), 5.65 (1H, s), 6.85 (1H, s), 7.34 (2H, br. s.), 7.39 (1H, dd, J=8.35, 1.10 Hz), 8.21 (1H, d, J=8.35 Hz), 8.26 (1H, s), 8.51 (1H, s); LC-MS: m/z=+454.05/456.05 (M+H)+.

Provenance & Evidence