Sodium Bicarbonate → 4-(6-(trifluoromethyl)-1H-indazol-4-yl)indolin-2-one

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A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.026 g, 0.096 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one (0.025 g, 0.096 mmol) and PdCl2(dppf) (3.53 mg, 4.82 μmol) in dioxane (4 mL) and aqueous saturated NaHCO3 (3 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 10 minutes. The product-containing fractions were combined and volatiles evaporated in vacuo to give a TFA salt of the title compound as a light brown solid (0.014 g, 0.044 mmol, 46%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.50 (s, 2H), 6.94 (d, J=7.58 Hz, 1H), 7.17 (dd, J=7.96, 0.88 Hz, 1H), 7.29-7.44 (m, 1H), 7.46-7.53 (m, 1H), 7.94 (s, 1H), 8.15 (s, 1H), 10.55 (s, 1H), 13.70 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C16H10F3N3O, 318.1. found 318.15.

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