Potassium Hydroxide → (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[6'-fluoro-2''-methyl-4-(trifluoromethyl)-1,1':3',1''-terphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one

Participants

Reaction Steps

(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[5′-bromo-2′-fluoro-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (79 mg, 0.123 mmol), (2-methylphenyl) boronic acid (25 mg, 0.182 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride dichloromethane adduct (10 mg, 0.0122 mmol), aqueous potassium hydroxide (82 μL, 3M, 0.246 mmol) and 1,4-dioxane (1 mL) were placed in a sealed tube and subjected to microwave irradiation at 140° C. for 15 minutes to complete the reaction. The crude reaction mixture was purified by preparative TLC on SiO2 (eluted with 30% Ethyl Acetate in hexanes) to afford (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[6′-fluoro-2″-methyl-4-(trifluoromethyl)-1,1′:3′,1″-terphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one as a ckcar glass. LCMS calc.=655.16; found=656.11 (M+1)+. 1H NMR signals are doubled because of atropisomerism 1H NMR (CDCl3, 500 MHz) δ 7.86 (s, 1H), 7.73 (s, 1H), 7.72-7.66 (m, 2H), 7.48 (d, J=8 Hz, 1H), 7.41-7.36 (m, 1H), 7.29-7.23 (m, 4H), 7.19-7.23 (m, 3H), 5.56 (br s, 1H), 4.96 (br s, 1H), 4.13 (br d, J=46.5 Hz, 1H), 3.83 (br d, J=43.5 Hz, 1H), 2.29 (s, 3H), 0.56, 0.51 (br s, 3H).

Provenance & Evidence