Water → Rac-[1-(3,4-dichloro-phenyl)-2-(3-fluoro-3'-methanesulfonyl-biphenyl-4-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Participants

Reaction Steps

To a solution of 0.450 g (0.943 mmol) rac-[2-(4-bromo-2-fluoro-phenyl)-1-(3,4-dichloro-phenyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester in 10.5 ml toluene/ethanol 19:1 were added 69 mg (0.094 mmol) PdCl2 (dppf), 0.238 g (2.83 mmol) sodium bicarbonate, 5 ml water and 212 mg (1.04 mmol) 3-methylsulfonylphenylboronic acid and the mixture heated to reflux for 18 h. The reaction mixture was cooled to ambient temperature, filtered through a Dicalite pad and the filtrated extracted with tertiary butyl methyl ether. The combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated. The crude product was purified by flash-chromatography over silica gel with a heptane/AcOEt gradient with 10-50% AcOEt: rac-[1-(3,4-dichloro-phenyl)-2-(3-fluoro-3′-methanesulfonyl-biphenyl-4-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester was obtained as colorless solid: MS (ISN): 550.2 and 552.2 (M−H)−.

Provenance & Evidence