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

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Reaction Steps

(4R,5R)-5-[2-iodo-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (INTERMEDIATE 12, 100 mg, 0.269 mmol), methyl 4′-methoxy-2-methyl-3′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-4-carboxylate (INTERMEDIATE 11, 124 mg, 0.323 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride dichloromethane adduct (44 mg, 0.054 mmol), aqueous potassium carbonate (270 μL, 2M, 0.538 mmol) and 1,4-dioxane (2 mL) were sealed in a microwave vessel. The vessel was irradiated by microwave at 140° C. for 30 minutes. LCMS of the aliquot indicated complete consumption of starting iodide. The crude mixture was purified by SiO2 (preparative TLC plates, 50% ethyl acetate in hexanes) to give a glassy residue. The residue was further purified by SiO2 (preparative TLC plates, 10% ethyl acetate in dichloromethane) to afford methyl 4′-methoxy-2-methyl-2″-[(4R,5R)-4-methyl-2-oxo-1,3-oxazolidin-5-yl]-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylate. LCMS calc.=499.16; found=500.08 (M+1).

Provenance & Evidence