反应详情

温度

60 °C

To a mixture of 3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-5,6-dihydrobenzo[d]isoxazol-7(4H)-one (850 mg, 2.6 mmol) and 4-fluoroaniline (877 mg, 7.89 mmol) in THF (10 mL) was added Ti(OPr-i)4 (823 mg, 2.9 mmol) and the reaction mixture was stirred at 60° C. overnight. The mixture was cooled to 0° C., and 10.0 mL of dry ethanol was added, followed by NaBH4 (149 mg, 3.4 mmol). The mixture was stirred for 1 hr, precipitate was removed by filtration and washed with ethyl acetate. The filtrate was partitioned between water and ethyl acetate. The aqueous phase was extracted with ethyl acetate. The combined organic phase was washed with brine, dried over MgSO4 and concentrated. The crude product was purified by silica gel chromatography using a gradient of 0-7% of MeOH in DCM to afford the 660 mg of the title product.

1. temperatureThe mixture was cooled to 0° C.
2. stirringThe mixture was stirred for 1 hr
3. customprecipitate was removed by filtration
4. washwashed with ethyl acetate
5. customThe filtrate was partitioned between water and ethyl acetate
6. extractionThe aqueous phase was extracted with ethyl acetate
7. washThe combined organic phase was washed with brine
8. dry with materialdried over MgSO4
9. concentrationconcentrated
10. customThe crude product was purified by silica gel chromatography