Sodium Bicarbonate → 2-methyl-3-(6-(trifluoromethyl)-1H-indazol-4-yl)pyridin-4-amine

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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), 3-bromo-2-methylpyridin-4-amine (0.078 g, 0.417 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 20% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 5 minutes. The volatiles were removed in vacuo to give a TFA salt of the title compound as clear oil (12 mg, 13%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.11 (s, 3H), 6.69 (br s, 1H), 6.90 (d, J=7.07 Hz, 1H), 7.38 (s, 1H), 8.01 (s, 1H), 8.08 (s, 1H), 8.17 (t, J=6.44 Hz, 1H), 13.51 (br s, 1H); ESI-MS m/z [M+H]+ calc'd for C14H11F3N4, 293.1. found 293.14.

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