反应详情

To a suspension of sodium hydride (60% in oil, 26.0 mg) in tetrahydrofuran (3 mL) was added tert-butyl {[5-(2-cyanopyridin-3-yl)-1H-pyrrol-3-yl]methyl}methylcarbamate (156 mg) at room temperature, and the mixture was stirred for 10 min. After stirring, 15-crown-5 (143 mg) and thiophene-3-sulfonyl chloride (138 mg) were added dropwise and the mixture was further stirred at room temperature for 15 min. Saturated aqueous ammonium chloride solution was added, and the mixture was concentrated under reduced pressure. The residue was extracted with ethyl acetate. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=6:1→3:2) to give the title compound as a pale-yellow oil (yield 201 mg, 88%).

1. stirringAfter stirring
2. stirringthe mixture was further stirred at room temperature for 15 min
3. concentrationthe mixture was concentrated under reduced pressure
4. extractionThe residue was extracted with ethyl acetate
5. extractionThe separated aqueous layer was extracted again with ethyl acetate
6. washThe combined organic layer was washed with saturated brine
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=6:1→3:2)