Water → (3-Amino-2-fluoro-phenyl)-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

HRID 60092노트

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HRID 60092 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[C:14]=3[F:22])=[O:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.O>O1CCCC1.C(OCC)(=O)C>[NH2:19][C:15]1[C:14]([F:22])=[C:13]([C:11]([C:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=3)[NH:8][CH:9]=2)=[O:12])[CH:18]=[CH:17][CH:16]=1

참가 물질

5

반응물 2

HCID 962WaterHCID 58368909(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-(2-fluoro-3-nitro-phenyl)-methanone

생성물 1

HCID 58368906(3-Amino-2-fluoro-phenyl)-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone수율 46.7%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매2회

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온도
60 °C

실험 절차

To (5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-(2-fluoro-3-nitro-phenyl)-methanone (18, 2.27 g, 6.23 mmol) in 200 mL of tetrahydrofuran and 200 mL of ethyl acetate, stannous chloride, dehydrate (4.85 g, 2.15 mmol) is added. The reaction is heated at 60° C. for 3 days, then 300 mL of water and 200 mL of ethyl acetate are added. The mixture is treated with celite and filtered. Brine is added, the organic layer is separated, dried over magnesium sulfate, filtered and the filtrate is concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with ethyl acetate and hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (19, 972 mg).

후처리

  1. additionThe mixture is treated with celite and
  2. filtrationfiltered
  3. additionBrine is added
  4. customthe organic layer is separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated under vacuum
  8. customThe resulting material is purified by silica gel column chromatography
  9. washeluting with ethyl acetate and hexane
  10. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-e58f7501039241dbbcddf1e084e1de49
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440969B2

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