Diisopropylamine → 5-(2,4-Difluorophenyl)pyridine-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromonicotinic acid (0.5 g, 2.48 mmol) in DMF (7.4 mL) and water (2.5 mL) were added (2,4-difluorophenyl)boronic acid (0.43 g, 2.72 mmol), palladium acetate (27.8 mg, 0.12 mmol), 3,3′,3″-phosphinidynetris (benzensulfonic acid) trisodium salt (0.21 g, 0.37 mmol) and diisopropylamine (1.23 mL, 8.66 mmol). The mixture was heated to 80° C. After 1.5 h, the mixture was cooled to ambient temperature and filtered. The filtrate was purified by reverse chromatography (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid). The product was converted to hydrochloride salt by adding HCl (2.0 M in ether) and concentrated to give the hydrochloride salt of the title compound (0.65 g). MS 236.0 (M+1).

Provenance & Evidence