反应详情

Methyl 4,5,6-trimethoxyindole-2-carboxylate (533 mg), bromobenzene (0.22 mL), copper oxide (64 mg) and potassium hydroxide (336 mg) were suspended in dry DMF (10 mL), and the suspension was refluxed and stirred for 6 hours under an argon atmosphere. After cooling, the reaction mixture was dissolved in water (100 mL) and filtered through celite. The filtrate was extracted with ethyl acetate, and the extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was dissolved in methanol (20 mL) and chloroform (20 mL), and water-soluble carbodiimide hydrochloride (192 mg) and N,N-dimethylaminopyridine (small amount) were added to the solution. The mixture was stirred overnight at room temperature. After concentrating the reaction mixture under reduced pressure, water was added to the residue to conduct extraction with ethyl acetate. The resultant organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by preparative TLC on silica gel (ethyl acetate:hexane=1:3) to obtain the title compound.

1. temperaturethe suspension was refluxed
2. temperatureAfter cooling
3. filtrationfiltered through celite
4. extractionThe filtrate was extracted with ethyl acetate
5. washthe extract was washed with water and saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. dissolutionThe residue was dissolved in methanol (20 mL)
9. additionchloroform (20 mL), and water-soluble carbodiimide hydrochloride (192 mg) and N,N-dimethylaminopyridine (small amount) were added to the solution
10. stirringThe mixture was stirred overnight at room temperature
11. concentrationAfter concentrating the reaction mixture under reduced pressure, water
12. additionwas added to the residue
13. extractionextraction with ethyl acetate
14. washThe resultant organic layer was washed with water and saturated brine
15. dry with materialdried over anhydrous magnesium sulfate
16. concentrationconcentrated under reduced pressure
17. customThe residue was purified by preparative TLC on silica gel (ethyl acetate:hexane=1:3)