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Trifluoroacetic acid → 3-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)aniline

HRID 2240220
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HRID 2240220 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[N:16](COCC[Si](C)(C)C)[CH:17]=[CH:18][C:11]=12)[NH2:5].FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH2:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[NH:16][CH:17]=[CH:18][C:11]=12)[NH2:5]
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참가 물질

4

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HCID 6422Trifluoroacetic acidHCID 593049903-Fluoro-4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]aniline

생성물 1

HCID 593050333-fluoro-4-(1H-pyrrolo[2,3-b]pyridin-4-ylmethyl)aniline

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

477 mg (1.00 mmol) of 3-fluoro-4-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]aniline are dissolved in 4 ml of dichloromethane. 4.0 ml of trifluoroacetic acid are added, and the mixture is stirred at RT for 2 hours. The solution is concentrated to dryness. The residue is taken up in 15 ml of THF, and 15 ml of an aqueous 1 M lithium hydroxide solution are added. The solution is stirred at RT for 20 hours and then concentrated, and water is added. The mixture is extracted with ethyl acetate. The extract is dried over sodium sulfate and the solvent is removed under reduced pressure. The residue is purified by preparative HPLC.

후처리

  1. concentrationThe solution is concentrated to dryness
  2. addition15 ml of an aqueous 1 M lithium hydroxide solution are added
  3. stirringThe solution is stirred at RT for 20 hours
  4. concentrationconcentrated
  5. additionwater is added
  6. extractionThe mixture is extracted with ethyl acetate
  7. dry with materialThe extract is dried over sodium sulfate
  8. customthe solvent is removed under reduced pressure
  9. customThe residue is purified by preparative HPLC

출처 및 근거

ORD 기록
ord-f05717f6828649bbb02c420a02c1bc50
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07723347B2

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