反应详情

To a solution of 7-amino-3-cyano-4-methyl-1H-indole (10 g, 58.4 mmol) in tetrahydrofuran (200 ml) were added pyridine (20 ml) and 3-cyanobenzenesulfonyl chloride (12.5 g), followed by stirring at room temperature for 3.5 hours. After further adding 2N hydrochloric acid (100 ml), extraction was performed with ethyl acetate. The organic layer was washed with water (twice) and brine in that order, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1-3:2). A mixed solvent of ethanol-hexane (1:2) was added thereto, and after sonication, the precipitate was collected by filtration and washed with a mixed solvent of ethanol-hexane (1:3). The mixture was dried overnight under reduced pressure to give the title compound (9.33 g, 27.7 mmol, 47% yield).

1. additionAfter further adding
2. extraction2N hydrochloric acid (100 ml), extraction
3. washThe organic layer was washed with water (twice) and brine in that order
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1-3:2)
7. additionA mixed solvent of ethanol-hexane (1:2) was added
8. customafter sonication
9. filtrationthe precipitate was collected by filtration
10. washwashed with a mixed solvent of ethanol-hexane (1:3)
11. customThe mixture was dried overnight under reduced pressure