4'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-carbaldehyde → Ethyl 3-[4-({[4'-(2-ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}amino)phenyl]-2-fluoropropanoate

Participants

Reaction Steps

To a solution of ethyl 3-(4-aminophenyl)-2-fluoropropanoate (400 mg, 1.89 mmol) and 4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-carbaldehyde (434 mg, 1.45 mmol) in toluene (25 mL) were added molecular sieves (0.4 nm, beads, 1.6 g), and the mixture was stirred at room temperature for 16 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in tetrahydrofuran (20 mL) and ethanol (20 mL), 10% palladium-carbon (50% water-containing product, 0.40 g) was added, and the mixture was stirred under a hydrogen atmosphere (balloon pressure) at room temperature for 3 hr. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-40% hexane/ethyl acetate) to give the title compound (320 mg, yield 45%) as a colorless oil.

Provenance & Evidence