Piperidine → 1-{[1-(2-aminopyrimidin-4-yl)-6-[(3R)-3-hydroxy-3-(pyrimidin-2-yl)but-1-yn-1-yl]-1H-indazol-3-yl]carbonyl}azetidin-3-ol

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To a pressure tube was added 1-{[1-(2-aminopyrimidin-4-yl)-6-iodo-1H-indazol-3-yl]carbonyl}azetidin-3-ol (150 mg, 0.34 mmol) followed by piperidine (2.0 mL), Pd(PPh3)4 (39.74 mg, 0.03 mmol), copper(I) iodide (6.5 mg, 0.03 mmol) and 2-(1,3-oxazol-2-yl)but-3-yn-2-ol (70.74 mg, 0.5 mmol). The reaction vessel was capped and stirred at 35° C. for 2.5 hr. The reaction mixture was concentrated in vacuo. DCM (5 mL×2) added and the mixture was concentration in vacuo. The crude material purified by column chromatography (elution with 1-10% MeOH in DCM) and was then triturated from a MeCN/Ether mixture (3:1) to give the title compound: 1H NMR (DMSO-d6, 500 MHz) delta 1.94 (3H, s), 3.87 (1H, dd, J=10.4, 3.9 Hz), 4.31-4.44 (2H, m), 4.51-4.64 (1H, m), 4.88 (1H, dd, J=9.9, 6.9 Hz), 5.83 (1H, d, J=6.5 Hz), 6.81 (1H, s), 7.12 (1H, d, J=5.5 Hz), 7.18 (2H, s), 7.24 (1H, s), 7.46 (1H, d, J=8.4 Hz), 8.16 (1H, s), 8.27 (1H, d, J=8.4 Hz), 8.37 (1H, d, J=5.5 Hz), 8.96 (1H, s). LC-MS: m/z+388.05 (M+H)+.

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