Sodium Bicarbonate → Trifluoroacetic acid

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A vial was charged with a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)-1H-indazole (0.1 g, 0.320 mmol), (4-bromo-1-methyl-1H-pyrazol-5-yl)methanol (0.086 g, 0.449 mmol) and PdCl2(dppf) (0.012 g, 0.016 mmol) in dioxane (8 mL) and aqueous saturated NaHCO3 (2 mL). The resulting light brown suspension was heated at 140° C. for 45 minutes in a microwave reactor. The reaction mixture was subsequently concentrated and the crude residue was purified by preparative HPLC, eluting with 30% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 6 minutes. The product-containing fractions were combined and volatiles removed in vacuo to give a TFA salt of the title compound as an off white solid (8 mg, 8%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.96 (s, 3H), 4.56 (d, J=4.80 Hz, 2H), 5.53 (t, J=4.93 Hz, 1H), 7.43 (s, 1H), 7.78-7.92 (m, 2H), 8.30 (s, 1H), 13.62 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C13H11F3N4O, 297.1. found 297.14.

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