Diisopropylamine → Methyl 5-(4-fluorophenyl)-6-oxo-1-(3-oxobutan-2-yl)-1,6-dihydropyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-bromo-6-oxo-1-(3-oxobutan-2-yl)-1,6-dihydropyridine-3-carboxylate (11.3 g, 37.4 mmol) in N,N-dimethylformamide (112 mL) and water (37 mL) were added 4-fluorophenylboronic acid (6.28 g, 44.9 mmol), palladium acetate (0.17 g, 0.75 mmol), 3,3′,3″-phosphinidynetris(benzenesulfonic acid) trisodium salt (1.28 g, 2.24 mmol) and diisopropylamine (13.3 mL, 94.0 mmol). The reaction mixture was heated to 80° C. After 30 min, the mixture was cooled to ambient temperature. Saturated aqueous sodium bicarbonate and water were added. The mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with water (3×), brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→80% dichloromethane/ethyl acetate) gave the title compound. MS 318.2 (M+1).

Provenance & Evidence