Sodium Carbonate → 4-phenyl-6-(trifluoromethyl)-1H-indazole

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A vessel was charged with 4-bromo-6-(trifluoromethyl)-1H-indazole (0.1 g, 0.377 mmol), phenylboronic acid (0.069 g, 0.566 mmol), PdCl2(dppf) (0.014 g, 0.019 mmol), and dioxane (3 mL). To the resulting slurry was added 2N aqueous sodium carbonate (0.377 mL, 0.755 mmol). The mixture was purged with nitrogen, heated in a microwave reactor at 120° C. for 30 minutes, and then filtered through a pad of Celite, which was rinsed with methanol. The solvent was removed in vacuo, and the resulting residue was taken up in DMSO and methanol (1:1) and was purified via acidic preparative HPLC (Waters SunFire C18, 5 μm, 30 mm ID×75 mm column), eluting with a gradient of 55-80% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA). The collected fractions were dried in vacuo to give a TFA salt of the title compound as a tan solid (35 mg, 35%). 1H NMR (400 MHz, CDCl3) δ ppm 7.43-7.62 (m, 4H), 7.71 (d, J=7.07 Hz, 2H), 7.83 (s, 1H), 8.23-8.38 (m, 1H), 8.47 (br s, 1H); ESI-MS m/z [M+H]+ calc'd for C14H9F3N2, 263.1. found 263.1.

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