1,2-Dimethoxyethane → HCID 68312317, compound

Participants

Reaction Conditions

Reaction Steps

A 20 mL microwave vial was charged with 6-(trifluoromethyl)pyridin-3-ylboronic acid (553 mg, 2.89 mmol), 2-bromo-3-fluoro-6-methylpyridine (500 mg, 2.63 mmol), bis(triphenylphosphine)palladium(II) chloride (92 mg, 0.132 mmol), and K2CO3 (727 mg, 5.26 mmol), followed by the addition of DME (9.0 mL), water (3.86 mL) and ethanol (2.57 mL). The reaction mixture was heated in the microwave at 120° C. for 10 minutes. To the reaction mixture was added 200 mL EtOAc, and washed with 200 mL water and 200 mL brine. The organic phase was separated, dried over Na2SO4, filtered, and concentrated. The residue was chromatographed on a Grace Reveleris 40 g column, eluted with 0-40% EtOAc in Hexanes (25 mL/min) to provide the title compound (7.47 mmol, 95% yield) as a white solid. MS (ESI+) m/z 257.1 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 9.24 (s, 1H), 8.59-8.52 (m, 1H), 8.07 (d, J=8.2, 1H), 7.84 (dd, J=11.1, 8.5, 1H), 7.46 (dd, J=8.5, 3.5, 1H), 2.57 (s, 3H).

Provenance & Evidence