2-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1.32 mmol, 370 mg), K3PO4 (3.04 mmol, 644 mg), and PdCl2(dppf).CH2Cl2 (0.10 mmol, 83 mg) was added to a solution of tert-butyl 4-((7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-iodopyrazolo[1,5-a]pyrimidin-5-yl)methyl)piperidine-1-carboxylate (Int-12e, 1.02 mmol, 726 mg) in dioxane (6 mL) and H2O (1 mL). The resulting solution was stirred at 100° C. under argon for 18 hours. The mixture was diluted with H2O and then extracted with ethyl acetate (x2). The combined organic layers were washed with brine and dried with Na2SO4. Evaporation and purification by column chromatography afforded tert-butyl 4-((7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)piperidine-1-carboxylate (Int-12f): LCMS tR=3.47 Min (5 min run, UV254nm). Mass calculated for, M+744.2, observed m/z 745.2 (M+H).
