반응 #46518

반응 방정식

3,3,5-tribromo-1,3-dihydropyrrolo[2,3-b]pyridin-2-one

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title compound

수율 32.0%

5-Bromo-1,3-dihydropyrrolo[2,3-b]pyridin-2-one

수율 32.0%

용매

acetic acid

반응 조건

후처리

1. 1
   온도was cooled by the use of an ice bath during the initial 30 minutes
2. 2
   여과After 5 hr the reaction was filtered through Celite®
3. 3
   세척the filter pad was washed with EtOAc
4. 4
   농축The filtrate was concentrated under vacuum
5. 5
   추출The neutralized aqueous filtrate was then extracted with EtOAc (2×200 mL)
6. 6
   건조the combined organic extracts were dried over Na2SO4
7. 7
   농축concentrated to a solid
8. 8
   세척The solid was washed with hexanes
9. 9
   기타dried under high vacuum

실험 절차

To a stirred solution of 3,3,5-tribromo-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (2.0 g, 5.4 mmole) in acetic acid (50 mL) at RT was added Zn metal. The reaction became exothermic and was cooled by the use of an ice bath during the initial 30 minutes. After 5 hr the reaction was filtered through Celite®, and the filter pad was washed with EtOAc. The filtrate was concentrated under vacuum and neutralized with saturated aqueous NaHCO3 solution. The neutralized aqueous filtrate was then extracted with EtOAc (2×200 mL), and the combined organic extracts were dried over Na2SO4 and concentrated to a solid. The solid was washed with hexanes and dried under high vacuum to give the title compound (0.36 g, 32%): MS (ES) m/e 215 (M+H)+. This was used without further purification.

출처