Sodium Bicarbonate → 4-(3,5-dimethyl-1-((3-methyloxetan-3-yl)methyl)-1H-pyrazol-4-yl)-6-(trifluoromethyl)-1H-indazole

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To a 5 mL vial equipped with a magnetic stir bar were added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole (41.6 mg, 0.133 mmol), 4-bromo-3,5-dimethyl-1-((3-methyloxetan-3-yl)methyl)-1H-pyrazole (51.8 mg, 0.2 mmol), sodium bicarbonate (0.285 mL, 0.533 mmol), PdCl2(dppf) (9.76 mg, 0.013 mmol), and dioxane (3 mL). The contents of the vial were stirred to give an orange suspension. The vial was sealed and then heated in a microwave reactor at 140° C. for 90 minutes. The reaction mixture was subsequently filtered and the product was purified by preparative HPLC, eluting with a gradient of 25-50% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA). The pure fractions were lyophilized to give a TFA salt of the title compound as a clear glass (6.9 mg, 11%). 1H NMR (400 MHz, CD3OD) δ ppm 1.46 (s, 3H), 2.37 (s, 6H), 3.71 (s, 2H), 4.31 (d, J=11.37 Hz, 2H), 4.58 (d, J=11.37 Hz, 2H), 7.39 (d, J=1.01 Hz, 1H), 8.04-8.06 (m, 1H), 8.07 (d, J=0.76 Hz, 1H); ESI-MS m/z [M+H]+ calc'd for C18H19F3N4O, 365.2. found 365.3.

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