Reaction Steps
To a 10-mL microwave vial were added 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-3-methyl-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (70 mg, 0.180 mmol), 1-methyl-4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl]piperazine (71.1 mg, 0.235 mmol), DMSO (2.0 mL) and sodium carbonate (0.271 mL, 0.541 mmol) and the mixture was degassed for 10 min under nitrogen. Bis(triphenylphosphine)palladium(II) chloride (10.13 mg, 0.014 mmol) was added and the contents were sealed. The mixture was irradiated (microwave) at 140° C. for 8 h. The reaction mixture was then quenched with water (5 mL) and filtered. The crude product was washed with water, dried, and then purified via silica gel chromatography (eluent: gradient of 0 to 15% (9:1 MeOH/NH4OH)/DCM). The resulting product was treated with MeOH and 1N HCl. The mixture was concentrated in vacuo, dried under high vacuum and collected as the HCl salt, 42 mg (36%). LCMS E-S (M+H)=529.0 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50 (d, 6 H), 2.13 (s, 3 H), 2.25 (s, 3 H), 2.42 (s, 3 H), 2.81 (d, J=4.55 Hz, 3 H), 3.03-3.21 (m, 2 H), 3.41 (br. s., 2 H), 3.52 (d, J=11.37 Hz, 2 H), 4.39 (d, J=5.05 Hz, 2 H), 4.56 (d, J=14.40 Hz, 2 H), 5.23 (quin, J=6.63 Hz, 1 H), 5.91 (s, 1 H), 7.19 (d, J=9.09 Hz, 1 H), 7.68 (s, 1 H), 8.50 (dd, J=9.09, 2.27 Hz, 1 H), 8.73 (t, J=4.93 Hz, 3 H), 8.98 (d, J=2.02 Hz, 3 H), 10.97-11.21 (m, 2 H)
