4-Bromo-6-(trifluoromethyl)-1H-indazole → 4-(6-chloro-2-methylpyridin-3-yl)-6-(trifluoromethyl)-1H-indazole

Participants

Reaction Conditions

Reaction Steps

The reaction was carried out in eight microwave vials. To each vial were added 4-bromo-6-(trifluoromethyl)-1H-indazole (0.5 g, 1.886 mmol), (6-chloro-2-methylpyridin-3-yl)boronic acid (0.3875 g, 2.264 mmol) and PdCl2(dppf) (0.069 g, 0.0944 mmol) in dioxane (12 mL) and aqueous saturated NaHCO3 (3 mL). The resulting light-brown suspensions were each heated at 140° C. for 60 minutes in a microwave reactor. The reaction mixtures were combined and concentrated and the crude residue was diluted with EtOAc and washed with water. The volatiles were removed via rotary evaporation and the product purified by CombiFlash® chromatography, eluting with a gradient of 0-100% EtOAc in heptane over a period of 180 minutes. The product-containing fractions were combined and the volatiles removed via rotary evaporation to give the title compound (3.56 g, 76%). ESI-MS m/z [M+H]+ calc'd for C14H9ClF3N3, 312.05. found 311.89.

Provenance & Evidence