Potassium Carbonate → methyl 2''-{(4R,5R)-3-[3,5-bis(trifluoromethyl)benzyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl}-4'-chloro-2-methyl-4''-(trifluoromethyl)-1,1':3',1''-terphenyl-4-carboxylate

Participants

Reaction Steps

(4R,5R)-3-[3,5-bis(trifluoromethyl)benzyl]-5-[2-iodo-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (103 mg, 0.172 mmol, in 515 μL toluene), methyl 4′-chloro-2-methyl-3′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-4-carboxylate (100 mg, 0.259 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride dichloromethane adduct (14 mg, 10%), aqueous potassium carbonate (344 μL, 2M, 0.688 mmol), and ethanol (2 mL) were sealed in a microwave vessel. The reaction mixture was irradiated by microwave at 140° C. for 45 minutes. LC/MS analysis indicated complete consumption of starting material. Crude material was purified by SiO2 (Prep-TLC 30% EtOAc/hex) to afford a yellow residue. The residue was further purified by a preparative reverse phase HPLC (Kromasil 100-5C18, 100×21.1 mm) eluting w/a MeCN (0.1% TFA, v/v)/H2O (0-1% TFA, v/v) gradient mixture affording methyl 2″-{(4R,5R)-3-[3,5-bis(trifluoromethyl)benzyl]-4-methyl-2-oxo-1,3-oxazolidin-5-yl}-4′-chloro-2-methyl-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylate. LCMS calc.=729.13; found=730.14 (M+1)+.

Provenance & Evidence