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 (0.05 g, 0.160 mmol), 5-bromopicolinamide (0.042 g, 0.208 mmol) and PdCl2(dppf) (5.86 mg, 8.01 μmol) 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 a gradient of 25-45% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 6 minutes. The volatiles were removed in vacuo to give a TFA salt of the title compound as an off white solid (19 mg, 0.062 mmol, 39%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.66 (s, 1H), 7.77 (br s, 1H), 8.06 (s, 1H), 8.14-8.33 (m, 1H), 8.37-8.49 (m, 1H), 9.00-9.08 (m, 1H), 13.84 (br s, 1H); ESI-MS m/z [M+H]+ calc'd for C14H9F3N4O, 307.1. found 307.15.

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