Sodium Bicarbonate → ethyl 2-(4-(6-(trifluoromethyl)-1H-indazol-4-yl)-1H-pyrazol-1-yl)acetate

Participants

Reaction Conditions

Reaction Steps

A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.3 g, 1.132 mmol), ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)acetate (0.349 g, 1.245 mmol) and PdCl2(dppf) (0.041 g, 0.057 mmol) in dioxane (10 mL) and aqueous saturated NaHCO3 (3 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 40-45% ACN (containing 0.035% TFA) in H2O (containing 0.05% TFA) over a period of 6.5 minutes. The product-containing fractions were combined and the volatiles were removed via rotary evaporation to give a TFA salt of the title compound as a light brown solid (0.14 g, 37%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.24 (t, J=7.07 Hz, 3H), 4.19 (q, J=7.16 Hz, 2H), 5.15 (s, 2H), 7.60 (d, J=1.01 Hz, 1H), 7.77 (s, 1H), 8.27 (d, J=0.76 Hz, 1H), 8.53 (s, 1H), 8.63 (s, 1H), 13.64 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C15H13F3N4O2, 339.1. found 339.

Provenance & Evidence