Example 71
A vessel was charged with N-[2,6-difluoro-3-[1-(oxan-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[3,4-b]pyridine-3-carbonyl]phenyl]propane-1-sulfonamide (88.0 mg, 0.149 mmol), 5-bromo-2-(trifluoromethyl)pyrimidine (37.2 mg, 0.164 mmol), potassium fluoride (26.0 mg, 0.447 mmol), bis(triphenylphosphine)palladium(II) dichloride (5.23 mg, 0.00745 mmol) and 0.5 mL 1,4-dioxane/water (4+1). The vessel was evacuated and filled with argon (3×) and heated to 60° C. for 2 h. The reaction was acidified with conc. HCl (0.3 mL), diluted with MeOH (0.2 mL) and heated to 60° C. overnight. After cooling, the reaction was diluted with EtOAc and water. The organic phase was evaporated and the product was purified by flash chromatography (DCM/EtOAc gradient, from 5% to 35% EtOAc) N-[2,6-difluoro-3-[5-[2-(trifluoromethyl)pyrimidin-5-yl]-1H-pyrazolo[3,4-b]pyridine-3-carbonyl]phenyl]propane-1-sulfonamide (42.0 mg, 0.0798 mmol, 54% yield).
Analytical Data:
TLC-MS (ESI−): m/z=505.1, 525.1 [M−H]−
