Dimethylformamide → HCID 86679181, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with (5-bromo-pyridin-3-yl)-methanol (376 mg, 2.0 mmol), 1-methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (intermediate A-1) (574 mg, 2.0 mmol) and DMF (4 mL). After purging the reaction mixture with argon, bis(triphenylphosphine)palladium(II)chloride (140 mg, 0.2 mmol) and 2 N aq. Na2CO3 solution (2.0 mL, 4 mmol) were added and the reaction was heated in the microwave at 120° C. for 50 min. The reaction mixture was diluted with EtOAc, filtered through Dicalite and washed with EtOAc (2×20 mL). The resulting filtrate was washed with brine, dried over anhydrous Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (198 mg, 74%) as a white solid. MS: 269.2 (M+H+).

Provenance & Evidence