Hydrogen Bromide → 6-{(Z)-1-Bromo-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-chloropyridin-2(1H)-one

HRID 70539노트

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HRID 70539 반응식
Br.[Br:2]/[C:3](/[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([O:18]C)[N:12]=1)=[CH:4]\[C@@H:5]1[NH:9][C:8](=[O:10])[CH2:7][CH2:6]1.O>O1CCOCC1>[Br:2]/[C:3](/[C:11]1[NH:12][C:13](=[O:18])[C:14]([Cl:17])=[CH:15][CH:16]=1)=[CH:4]\[C@H:5]1[CH2:6][CH2:7][C:8](=[O:10])[NH:9]1

참가 물질

5

반응물 3

HCID 260Hydrogen BromideHCID 962WaterHCID 58452317(5R)-5-[(Z)-2-bromo-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one

생성물 1

HCID 584524336-{(Z)-1-Bromo-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-chloropyridin-2(1H)-one수율 37%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
65 °C

실험 절차

48% hydrobromic acid (2 mL) was added to a solution of (5R)-5-[(Z)-2-bromo-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one (115 mg) in 1,4-dioxane (3 mL), and the mixture was stirred at 65° C. for one hour. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=10:0→4:1) to give the title compound as a colorless powder (40 mg, 37%).

후처리

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=10:0→4:1)

출처 및 근거

ORD 기록
ord-d463d54529ec456088cf0930fbb68622
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822503B2

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