Diisopropylamine → Methyl 5-(4-fluorophenyl)-6-hydroxynicotinate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 5-bromo-6-oxo-1,6-dihydropyridine-3-carboxylate (0.50 g, 2.16 mmol) in DMF (8.1 mL) and water 2.7 mL) were added (4-fluorophenyl)boronic acid (0.38 g, 2.69 mmol), palladium(II) acetate (36.3 mg, 0.16 mmol), tris(3-sulfonatophenyl)phosphine hydrate sodium salt (0.31 g, 0.49 mmol) and diisopropylamine (1.54 mL, 10.8 mmol). The mixture was heated in the microwave reactor at 125° C. for 15 min. The mixture was filtered and water was added to the filtrate. The mixture was extracted with ethyl acetate and the organic layer was washed with water (3×), brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% dichloromethane→70% dichloromethane/ethyl acetate) gave the title compound (0.35 g). MS 248.1 (M+1).

Provenance & Evidence