Water → 5-Dibenzylamino-4-fluoro-isophthalic acid 3-ethyl ester

Participants

Reaction Conditions

Reaction Steps

Combine 5-bromo-3-dibenzylamino-2-fluorobenzoic acid ethyl ester (4.74 g, 10.7 mmol), palladium (II) acetate (0.72 g, 3.20 mmol), 1,4-bis(diphenylphosphino)butane (2.84 g, 6.66 mmol), triethylamine (7.90 mL, 56.7 mmol), DMSO (150 mL), tert-butyl alcohol (100 mL), and water (0.50 mL, 27.8 mmol). Place mixture in a container pressurized to 100 psi with carbon monoxide and heat at 80° C. for 24 h. Filter the reaction mixture over a pad of filtering agent. Pour the filtrate into water (500 mL), acidify with 5 N HCl and extract (2×500 mL) with ethyl acetate. Dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 4:96 methanol:dichloromethane) to give the title compound as a solid (2.40 g, 55%).

Provenance & Evidence