Potassium Carbonate → 4-(5-fluoropyridin-2-yl)-N-methoxy-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

Palladium tetrakis(triphenylphosphine) (1.38 g, 1.2 mmol) was added to a degassed, ambient temperature solution of 2-bromo-5-fluoropyridine (5 g, 28.4 mmol) and (4-{[methoxy(methyl)amino]carbonyl}phenyl)boronic acid (5 g, 23.9 mmol) and potassium carbonate (4.3 g, 31.1 mmol) in toluene/methanol (9.5:1) (105 mL). After stirring at 90° C. for 1.5 hr, the reaction mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-80% ethyl acetate/hexane afforded 4-(5-fluoropyridin-2-yl)-N-methoxy-N-methylbenzamide.

Provenance & Evidence