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

HRID 60092

反応式

HRID 60092 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e58f7501039241dbbcddf1e084e1de49
出典データセット
uspto-grants-2016_09
特許番号
US09440969B2

関連ノート

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