反応 #46518

反応方程式

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

→

title compound

収率 32.0%

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

収率 32.0%

溶媒

acetic acid

反応条件

後処理

1. 1
   温度was cooled by the use of an ice bath during the initial 30 minutes
2. 2
   ろ過After 5 hr the reaction was filtered through Celite®
3. 3
   洗浄the filter pad was washed with EtOAc
4. 4
   濃縮The filtrate was concentrated under vacuum
5. 5
   抽出The neutralized aqueous filtrate was then extracted with EtOAc (2×200 mL)
6. 6
   乾燥the combined organic extracts were dried over Na2SO4
7. 7
   濃縮concentrated to a solid
8. 8
   洗浄The solid was washed with hexanes
9. 9
   その他dried under high vacuum

実験手順

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.

出典