Sodium Carbonate → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

To 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-iodo-6-methylpyridin-2-amine (0.025 g, 0.107 mmol) and PdCl2(dppf) (0.012 g, 0.016 mmol) in dioxane (1.5 mL) was added 2N sodium carbonate (0.160 mL, 0.320 mmol). The reaction mixture was heated in a microwave reactor at 130° C. for 50 minutes. LCMS showed incomplete conversion of the starting material, so the reaction mixture was heated at 130° C. for an additional 50 minutes. LCMS again showed incomplete conversion. More catalyst was added, and the reaction mixture was again heated at 130° C. for 50 minutes. The reaction mixture was subsequently filtered through a microfiltration frit, which was rinsed with methanol. The solvents were removed in vacuo. The residue was taken up in DMSO and methanol (1:1) and was purified by preparative HPLC, eluting with 25% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA). The product-containing fractions were dried under vacuum to give a TFA salt of the title compound as a tan film (12 mg, 26%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.32 (s, 3H), 6.94 (d, J=9.35 Hz, 1H), 7.37 (s, 1H), 7.97 (d, J=8.84 Hz, 1H), 8.02 (s, 1H), 8.14 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C14H11F3N4, 293.1. found 293.2.

Provenance & Evidence