反应详情

In a round bottom flask, combine 4-(1-Oxo-indan-5-yloxy)-benzamide (Intermediate 24, 45.0 mg, 0.17 mmol), m-Fluorophenethylamine (33 uL, 0.25 mmol), THF (5 mL), and Ti(OiPr)4 (0.1 mL, 0.27 mmol) at 0° C. under nitrogen atmosphere. Stir the reaction for 3 hours then add TiCl4 (0.3 mL, 0.27 mmol) at 0° C. For the next 2 hours, warm the reaction to room temperature and then add BH3SMe2 (0.09 mL, 0.17 mmol). Stir the reaction at room temperature for 12 hours, then add 1N NaOH (aq) and stir for 2 hours. Centrifuge and decant the reaction into a separatory funnel and wash the organic phase with water and dry over Na2SO4. Concentrate the reaction under reduced pressure and purify using reverse phase chromatography (5% to 95% 0.001% TFA buffer in acetonitrile/water) to afford 3.5 mg, 0.01 mmol (6% yield) of the title compound:

1. customIn a round bottom flask, combine
2. customat 0° C.
3. customthe reaction for 3 hours
4. customat 0° C
5. temperatureFor the next 2 hours, warm
6. customthe reaction to room temperature
7. stirringStir
8. customthe reaction at room temperature for 12 hours
9. stirringstir for 2 hours
10. customCentrifuge and decant
11. customthe reaction into a separatory funnel
12. washwash the organic phase with water
13. dry with materialdry over Na2SO4
14. concentrationConcentrate
15. customthe reaction under reduced pressure
16. custompurify