反应详情

温度

115 °C

To a suspension of 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-propionic acid ethyl ester (29.2 g), (+)-4-chloro-2-fluoro-9-trifluoromethyl-9H-fluoren-9-ol (20.4 g), and sodium hydrogen carbonate (11.1 g) in toluene/water (200 ml/66 ml) were added palladium acetate (743 mg) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (2.72 g) at room temperature, and the mixture was stirred at 115° C. for 8 hr. To the reaction mixture were added activated carbon (10 g) and Celite (10 g) at room temperature and the mixture was stirred for 1 hr. The mixture was filtered through celite, and the solid was washed with toluene (100 ml). The filtrate was partitioned, and the aqueous layer was extracted with toluene (60 ml). The combined organic layer was washed 3 times with water (100 ml), and once with saturated brine (100 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. To a solution of the obtained residue in toluene/ethyl acetate (3/1, 130 ml) was added silica gel (40 g), and the mixture was stirred at room temperature for 1 hr. The mixture was filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1 to 2/1) to give the title compound (27.9 g).

1. additionTo the reaction mixture were added activated carbon (10 g) and Celite (10 g) at room temperature
2. stirringthe mixture was stirred for 1 hr
3. filtrationThe mixture was filtered through celite
4. washthe solid was washed with toluene (100 ml)
5. customThe filtrate was partitioned
6. extractionthe aqueous layer was extracted with toluene (60 ml)
7. washThe combined organic layer was washed 3 times with water (100 ml)
8. dry with materialonce with saturated brine (100 ml), dried over anhydrous sodium sulfate
9. concentrationconcentrated under reduced pressure
10. additionTo a solution of the obtained residue in toluene/ethyl acetate (3/1, 130 ml) was added silica gel (40 g)
11. stirringthe mixture was stirred at room temperature for 1 hr
12. filtrationThe mixture was filtered
13. concentrationconcentrated under reduced pressure
14. customThe obtained residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1 to 2/1)