反应详情

温度

100 °C

In a tube were placed 2-bromo-6-isopropenylpyridine (17.5 mg, 0.0878 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 (26.2 mg, 0.0439 mmol), DME (190 μL), EtOH (62 μL), and 1M aqueous Na2CO3 (100 μL, 0.1 mmol). The mixture was degassed with N2. Next, Pd(PPh3)4 (9 mg, 7.8×10−3 mmol) was added and the mixture was degassed again with N2. The tube was sealed and heated at 100° C. for 2 hours. The reaction was then cooled to room temperature, diluted with EtOAc (50 mL), and washed with water and brine (15 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (5 to 25% EtOAc/hexanes) afforded (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-(6-isopropenylpyridine-2-yl)-5-(trifluoromethyl)benzyl]-4-methyl-1,3-oxazolidin-2-one. Rf=0.15 (15% EtOAc/hexanes). LCMS=589.1 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.81-7.85 (m, 2H), 7.74 (s, 1H), 7.69-7.69 (m, 3H), 7.58 (d, J=8.0 Hz, 1H), 7.53 (d, J=7.7 Hz, 1H), 7.34 (d, J=7.6 Hz, 1H), 5.94 (s, 1H), 5.48 (d, J=7.7 Hz, 1H), 5.36 (s, 1H), 5.06 (d, J=16.0 Hz, 1H), 4.47 (d, J=16.1 Hz, 1H), 3.91 (m, 1H), 2.23 (s, 3H), 0.50 (d, J=6.6 Hz, 3H).

1. customIn a tube were placed
2. customThe mixture was degassed with N2
3. customthe mixture was degassed again with N2
4. customThe tube was sealed
5. temperatureThe reaction was then cooled to room temperature
6. additiondiluted with EtOAc (50 mL)
7. washwashed with water and brine (15 mL each)
8. dry with materialThe organic layer was dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customPurification of the residue by flash chromatography on silica gel (5 to 25% EtOAc/hexanes)