Sodium hydride → Tert-butyl 2-(6-fluoro-2,3-dioxoindolin-1-yl)acetate

HRID 571261노트

반응식

HRID 571261 반응식
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:12])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18]>CN(C=O)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:12])[C:7](=[O:11])[N:8]2[CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 3739056-Fluoroisatin

생성물 1

HCID 86681676Tert-butyl 2-(6-fluoro-2,3-dioxoindolin-1-yl)acetate수율 65%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 6-fluoroindoline-2,3-dione (2 g, 12.11 mmol) in dry DMF (100 ml) was cooled to 0° C., and NaH (60% w/w dispersion in mineral oil; 0.484 g, 12.11 mmol) was added portion wise over 10 minutes. The mixture was stirred at the same temperature for 10 minutes, then tert-butyl 2-bromoacetate (1.788 ml, 12.11 mmol) was added drop wise. The mixture was left warm to room temperature and stirred for 2 hours. DMF was evaporated under vacuum, and the crude was portioned between ethyl acetate (50 ml) and aqueous 1N HCl (40 ml). The aqueous phase was extracted with ethyl acetate (2×50 ml), and the combined organic layers were dried over sodium sulfate, filtered and concentrate under vacuum. The crude was purified by flash chromatography on silica gel cartridge (petroleum ether:ethyl acetate=80:20) affording tert-butyl 2-(6-fluoro-2,3-dioxoindolin-1-yl)acetate

후처리

  1. waitThe mixture was left
  2. stirringstirred for 2 hours
  3. customDMF was evaporated under vacuum
  4. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrate under vacuum
  8. customThe crude was purified by flash chromatography on silica gel cartridge (petroleum ether:ethyl acetate=80:20)

출처 및 근거

ORD 기록
ord-606c6d699f024aacad8bba7883088d72
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09024027B2

반응 노트

불러오는 중…