反应详情

To the suspension of {2-[3-(1H-indol-4-yl)-phenyl]-ethyl}-dimethyl-amine (600 mg, 2.2 mmol) in t-BuOH:ethanol:acetic acid (14.5 mL:8.8 mL:10.5 mL) was added pyridinium tribromide (2.3 g, 6.6 mmol) portionwise. The mixture was stirred at room temperature for 3 hours, and then to the mixture was added acetic acid (9.24 mL). Water (0.32 mL) and zinc dust (2.2 g, 61.2 mmol) was added to the reaction mixture portionwise. After stirring for one hour, any unreacted zinc was filtered off and most of the solvent was removed under reduced pressure. The residue was diluted with ethyl acetate, washed with water (3×), sat. NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was dissolved in methanol (10 mL) and hydrogenated using 10% Pd—C for overnight. The reaction was filtered through celite and the filtrate was concentrated. The residue was purified on a silica gel column to give 4-[3-(2-dimethylamino-ethyl)-phenyl]-1,3-dihydro-indol-2-one

1. stirringAfter stirring for one hour
2. filtrationany unreacted zinc was filtered off and most of the solvent
3. customwas removed under reduced pressure
4. additionThe residue was diluted with ethyl acetate
5. washwashed with water (3×), sat. NaHCO3, brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. dissolutionThe residue was dissolved in methanol (10 mL)
9. customfor overnight
10. filtrationThe reaction was filtered through celite
11. concentrationthe filtrate was concentrated
12. customThe residue was purified on a silica gel column