反应详情

A mixture of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-{[2′-methoxy-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)biphenyl-2-yl]methyl}-4-methyl-1,3-oxazolidin-2-one (60 mg, 0.085 mmol), methyl 4-bromo-3-methylbenzoate (29 mg, 0.128 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride dichloromethane adduct (28 mg, 30%), aqueous potassium hydroxide (57 μL, 3M, 0.171 mmol) and 1,4-dioxane (1 mL) was placed in a sealed tube and subjected to microwave irradiation at 140° C. for 15 minutes. The crude reaction was purified by preparative TLC on SiO2 (eluted with 30% EtOAc in hexanes) to afford methyl 2″-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4′-methoxy-2-methyl-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylate as a solid foam. LCMS calc.=725.18; found=726.49 (M+1)+. 1H NMR signals are doubled because of atropoisomerism. 1H NMR (CDCl3, 500 MHz) 7.94 (d, J=8.5 Hz, 1H), 7.88-7.83 (m, 2H), 7.71 (s, 0.5H), 7.69 (s, 0.5H), 7.68-7.60 (m, 2H), 7.45-7.39 (m, 2H), 7.38, 7.37 (d, J=2 Hz, 1H), 7.28 (d, J=8 Hz, 0.5H), 7.24 (d, J=8 Hz, 0.5H), 7.14 (d, J=2 Hz, 1H), 7.07 (t, J=8 Hz, 1H), 5.58 (d, J=8.5 Hz, 0.5H), 5.28 (d, J=8 Hz, 0.5H), 4.96 (d, J=10 Hz, 0.5H), 4.93 (d, J=9.5 Hz, 0.5H), 4.16 (d, J=15.5 Hz, 0.5H), 3.96 (d, J=16 Hz, 0.5H), 3.92 (s, 3H), 3.86 (s, 3H), 3.82-3.93 (m, 1H), 2.37 (s, 1.5H), 2.31 (s, 1.5H), 0.54 (d, J=6.5 Hz, 1.5H), 0.42 (d, J=6.5 Hz, 1.5H).

1. customwas placed in a sealed tube
2. customirradiation at 140° C. for 15 minutes
3. customThe crude reaction
4. customwas purified by preparative TLC on SiO2 (eluted with 30% EtOAc in hexanes)