反应详情

温度

80 °C

Para-toluenesulfonic acid (76 mg, 0.43 mmol) was added to a solution of 5-(3-fluorophenyl)benzofuran-3(2H)-one (212 mg, 0.935 mmol) and isopropyl 2-(3-aminophenoxyl)acetate (202 mg, 0.964 mmol) in methanol (4 mL) at 25° C. The reaction was heated in an 80° C. oil bath and allowed to stir overnight for approximately 16 hours. The reaction was cooled to room temperature and concentrated in vacuo. The mixture was then dissolved in concentrated acetic acid (2 mL) and cooled to 0° C. Sodium cyanoborohydride (386 mg, 6.13 mmol) was added and the solution was stirred for 4 hours at room temperature. The reaction was quenched with saturated aqueous NaHCO3 (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The resulting crude residue was purified by combiflash (12 g column, hexanes→100% ethyl acetate/hexanes, gradient) to afford 22 mg (6%) of isopropyl 2-(3-((5-(3-fluorophenyl)-2,3-dihydrobenzofuran-3-yl)amino)phenoxy)acetate.

1. temperatureThe reaction was cooled to room temperature
2. concentrationconcentrated in vacuo
3. dissolutionThe mixture was then dissolved in concentrated acetic acid (2 mL)
4. temperaturecooled to 0° C
5. stirringthe solution was stirred for 4 hours at room temperature
6. customThe reaction was quenched with saturated aqueous NaHCO3 (50 mL)
7. extractionextracted with ethyl acetate (3×50 mL)
8. dry with materialThe combined organic extracts were dried (Na2SO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe resulting crude residue was purified by combiflash (12 g column, hexanes→100% ethyl acetate/hexanes, gradient)