Sodium Bicarbonate → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

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), N-(5-bromo-6-methylpyridin-2-yl)methanesulfonamide (0.170 g, 0.641 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 30% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 8 minutes. The product-containing fractions were combined and the volatiles were removed in vacuo to give a TFA salt of the title compound as an off white solid (0.039 g, 33%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.30 (s, 3H), 3.31 (br s, 3H), 7.02 (d, J=8.08 Hz, 1H), 7.32 (d, J=1.01 Hz, 1H), 7.76 (d, J=8.34 Hz, 1H), 7.97 (s, 1H), 8.02 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C15H13F3N4O2S, 371.1. found 371.17.

Provenance & Evidence