反应详情

温度

90 °C

In a tube were placed (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(4-bromo-1,3-thiazol-2-yl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one (46.0 mg, 0.073 mmol), methyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (30 mg, 0.11 mmol), 1,1′-bis(di-t-butylphosphino)ferrocene palladium dichloride (5 mg, 7.3×10−3 mmol), THF (1 mL) and 1M K2CO3 (1 mL, 1 mmol). The mixture was degassed with N2, the tube was sealed, and the reaction was heated to 90° C. for 90 minutes. The reaction was cooled to room temperature and diluted with EtOAc (30 mL). The organic layer was washed with water and brine (10 mL) each, dried over Na2SO4, filtered and concentrated. Purification of the residue by flash chromatography on silica gel (5 to 40% EtOAc/hexanes) afforded methyl 4-{2-[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethyl)phenyl]-1,3-thiazol-4-yl}-3-methylbenzoate. Rf=0.29 (25% EtOAc/hexanes). LCMS=702.9 (M+1)+. 1H NMR (CDCl3, 600 MHz) δ 7.97 (s, 1H), 7.92 (dd, J=8.0, 1.4 Hz, 1H), 7.85-7.86 (m, 3H), 7.69-7.72 (m, 4H), 7.53 (s, 1H), 5.66 (d, J=8.0 Hz, 1H), 5.11 (d, J=16.2 Hz, 1H), 4.95 (d, J=16.2 Hz, 1H), 4.11 (m, 1H), 3.93 (s, 3H), 2.54 (s, 3H), 0.60 (d, J=6.6 Hz, 3H).

1. customIn a tube were placed
2. customThe mixture was degassed with N2
3. customthe tube was sealed
4. temperatureThe reaction was cooled to room temperature
5. additiondiluted with EtOAc (30 mL)
6. washThe organic layer was washed with water and brine (10 mL) each,
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customPurification of the residue by flash chromatography on silica gel (5 to 40% EtOAc/hexanes)