4-Bromo-6-(trifluoromethyl)-1H-indazole → methyl 2-(4-methoxy-3-(6-(trifluoromethyl)-1H-indazol-4-yl)phenyl)acetate

Participants

Reaction Conditions

Reaction Steps

A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.433 g, 1.633 mmol), methyl 2-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate (0.5 g, 1.633 mmol) and PdCl2(dppf) (0.060 g, 0.082 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. The crude residue was dissolved in EtOAc and was washed with water and brine, concentrated, and purified by CombiFlash® chromatography (0-35% MeOH in DCM). The product-containing fractions were combined and concentrated by rotary evaporation to give the title compound (0.47 g, 79%). ESI-MS m/z [M+H]+ calc'd for C18H15F3N2O3, 365.1. found 365.2.

Provenance & Evidence