2-Methoxy-4-methylpyridine-5-boronic acid → HCID 89783103, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.1 g, 0.377 mmol), (6-methoxy-4-methylpyridin-3-yl)boronic acid (0.082 g, 0.491 mmol) and PdCl2(dppf) (0.014 g, 0.019 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 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 solvent was removed on a rotary evaporator. The crude product was extracted into DCM, was washed sequentially with aqueous saturated NaHCO3, water, and brine, and was dried over Na2SO4. The volatiles were removed in vacuo to give the title compound as a white solid (0.053 g, 0.172 mmol, 46%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.14 (s, 3H), 3.91 (s, 3H), 6.88 (s, 1H), 7.29 (s, 1H), 7.97 (s, 2H), 8.12 (s, 1H), 13.71 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C15H12F3N3O, 308.1. found 308.15.

Provenance & Evidence