Sodium Bicarbonate → 4-(2-methoxypyrimidin-5-yl)-6-(trifluoromethyl)-1H-indazole

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A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.1 g, 0.377 mmol), (2-methoxypyrimidin-5-yl)boronic acid (0.076 g, 0.491 mmol) and PdCl2(dppf) (0.014 g, 0.019 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 a gradient of 35-40% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 8 minutes. The volatiles were removed in vacuo to give a TFA salt of the title compound as white solid (0.043 g, 39%). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.03 (s, 3H), 7.60 (d, J=1.01 Hz, 1H), 8.00 (s, 1H), 8.34-8.52 (m, 1H), 9.06 (s, 2H); ESI-MS m/z [M+1-1]′ calc'd for C13H9F3N4O, 295.1. found 295.15.

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