(2-Methoxy-5-(methoxycarbonyl)phenyl)boronic acid → HCID 89783141, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with a mixture of 4-bromo-6-(trifluoromethyl)-1H-indazole (0.631 g, 2.381 mmol), (2-methoxy-5-(methoxycarbonyl)phenyl)boronic acid (0.5 g, 2.381 mmol) and PdCl2(dppf) (0.087 g, 0.119 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 diluted with DCM and washed with water, concentrated, and then purified by CombiFlash® chromatography, eluting with a gradient of 0-40% MeOH in DCM over a period of 200 minutes. The product-containing fractions were combined and concentrated to give the title compound as a light brown solid (0.592 g, 71.0%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.85 (s, 3H), 3.84 (s, 3H), 7.21-7.46 (m, 2H), 7.89-7.99 (m, 3H), 8.10 (dd, J=8.59, 2.27 Hz, 1H), 13.62 (s, 1H); ESI-MS m/z [M+H]+ calc'd for C17H13F3N2O3, 351.1. found 351.16.

Provenance & Evidence