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Potassium Carbonate → Benzenamine,4-[(6-chloro-1h-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3,5-difluoro-

HRID 2192147
ノート
印刷プレビュー

反応式

HRID 2192147 の反応式
[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[C:4]([N+]([O-])=O)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].S(S([O-])=O)([O-])=O.[Na+].[Na+].Cl.[NH2:29][C:30]1[CH:35]=[C:34]([F:36])[C:33]([OH:37])=[C:32]([F:38])[CH:31]=1>CS(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][CH:9]=[CH:10][C:5]2=[C:4]([O:37][C:33]2[C:34]([F:36])=[CH:35][C:30]([NH2:29])=[CH:31][C:32]=2[F:38])[CH:3]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 179793386-chloro-4-nitro-1H-pyrrolo[2,3-b]pyridineHCID 229263204-Amino-2,6-difluorophenol hydrochloride

生成物 1

HCID 17979280Benzenamine,4-[(6-chloro-1h-pyrrolo[2,3-b]pyridin-4-yl)oxy]-3,5-difluoro-

試薬・触媒・溶媒 2

HCID 679
Dimethyl Sulfoxide
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

664 mg (3.36 mmol) of 6-chloro-4-nitro-1H-pyrrolo[2,3-b]pyridine, 1.39 g (10.1 mmol) of powdered potassium carbonate and 877 mg (5.04 mmol) of sodium dithionite are suspended in 10 ml of DMSO. The mixture is degassed, and 915 mg (5.04 mmol) of 4-amino-2,6-difluorophenol hydrochloride are added. The mixture is heated at 120° C. for 4 hours. After addition of ethyl acetate, the mixture is filtered off with suction through celite, and the celite is washed with ethyl acetate. The filtrate is shaken three times with saturated sodium bicarbonate solution and with saturated, sodium chloride solution. The filtrate is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is purified by column chromatography (silica gel 60, mobile phase: dichloromethane/methanol=50:1).

後処理

  1. customThe mixture is degassed
  2. filtrationthe mixture is filtered off with suction through celite
  3. washthe celite is washed with ethyl acetate
  4. dry with materialThe filtrate is dried over sodium sulfate
  5. customthe solvent is removed under reduced pressure
  6. customThe residue is purified by column chromatography (silica gel 60, mobile phase: dichloromethane/methanol=50:1)

出典と根拠

ORDレコード
ord-948cb4dc263042fbab3cddff008d2b7a
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08329716B2

反応ノート

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