Sodium Carbonate → Methyl 2''-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-6'-fluoro-4'-methoxy-3-methyl-4''-(trifluoromethyl)-1,1':3',1''-terphenyl-4-carboxylate

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Reaction Steps

methyl 2′-fluoro-5′-iodo-4′-methoxy-3-methylbiphenyl-4-carboxylate (135 mg, 0.337 mmol), (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)benzyl]-1,3-oxazolidin-2-one (INTERMEDIATE 9, 403 mg, 0.675 mmol, dissolved in 4.75 mL 1,4-dioxane), sodium carbonate (337 μL, aq., 2M, 0.674 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride dichloromethane adduct (55 mg, 0.07 mmol) were heated in an 80° C. oil bath for 2 hours then allowed to cooled to ambient overnight. Added additional (45,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-3-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)benzyl]-1,3-oxazolidin-2-one (INTERMEDIATE 9, 200 mg, 0.335 mmol, dissolved in 2.35 mL 1,4-dioxane) and resumed heating for 2 more hours. Reaction aliquot indicated the presence of M+23 (LCMS). Crude mixture was cooled, dried/Na2SO4 and deposited on prep-TLC plates (SiO2). The plates were developed by a 30% DCM/hex mixture to afford a green oil of 350 mg. The green oil was further purified by prep-TLC (SiO2, 30% DCM/hexanes) to afford a green glass. The green oil/glass was further purified by prep-TLC (SiO2, 20% EtOAc/hexanes) to afford the title compound. LCMS (ESI) calc.=743.17; found=744 (M+1)+.

Provenance & Evidence