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Chlorosuccinimide → N-{4-[(3-Chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]-3-fluorophenyl}-2,2,2-trifluoroacetamide

HRID 2240245
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HRID 2240245 반응식
[F:1][C:2]([F:32])([F:31])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:18]=[CH:17][N:16]=[C:15]3[N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:20]=[CH:21][C:14]=23)=[C:8]([F:30])[CH:7]=1)=[O:4].[Cl:33]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.O.ClCCl>[Cl:33][C:21]1[C:14]2[C:15](=[N:16][CH:17]=[CH:18][C:13]=2[CH2:12][C:9]2[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[C:2]([F:1])([F:31])[F:32])=[CH:7][C:8]=2[F:30])[N:19]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:27])([CH3:28])[CH3:29])[CH:20]=1
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참가 물질

6

반응물 2

HCID 31398ChlorosuccinimideHCID 593050202,2,2-trifluoro-N-{3-fluoro-4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]phenyl}acetamide

생성물 1

HCID 59305018N-{4-[(3-Chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]-3-fluorophenyl}-2,2,2-trifluoroacetamide

시약·촉매·용매 3

HCID 962Water용매
HCID 5943
Carbon Tetrachloride
용매
HCID 6344Dichloromethane용매

실험 절차

550 mg (1.07 mmol) of 2,2,2-trifluoro-N-{3-fluoro-4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]phenyl}acetamide and 143 mg (1.07 mmol) of N-chlorosuccinimide in 23 ml of carbon tetrachloride are heated at reflux for 20 min. After cooling, the mixture is diluted with water in dichloromethane and extracted. The organic phase is separated off, dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (mobile phase: dichloromethane with increasing amounts of methanol).

후처리

  1. temperatureat reflux for 20 min
  2. temperatureAfter cooling
  3. extractionextracted
  4. customThe organic phase is separated off
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by column chromatography on silica gel (mobile phase: dichloromethane with increasing amounts of methanol)

출처 및 근거

ORD 기록
ord-349d1a57e9ad43828d95602b1b4b0584
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07723347B2

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