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Dichloromethane → 5-Chloro-4-fluoro-1H-pyrrolo[2,3-B]pyridine

HRID 408173
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HRID 408173 반응식
[Cl:1][C:2]1[C:3]([F:21])=[C:4]2[CH:10]=[CH:9][N:8]([Si](C(C)C)(C(C)C)C(C)C)[C:5]2=[N:6][CH:7]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(Cl)Cl>C1COCC1>[Cl:1][C:2]1[C:3]([F:21])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1
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참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 2724141Tetrabutylammonium FluorideHCID 602052735-Chloro-4-fluoro-1-(tris(1-methylethyl)silyl)-1H-pyrrolo(2,3-b)pyridine

생성물 1

HCID 534129535-Chloro-4-fluoro-1H-pyrrolo[2,3-B]pyridine수율 89.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

5-Chloro-4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (3.0 g, 9.2 mmol) in THF (15 mL) at 0° C. was treated dropwise with TBAF (10.1 mL, 10.1 mmol). After 30 minutes, the reaction was quenched with saturated aqueous NaHCO3 and extracted into CH2Cl2. The combined organic fractions were dried (MgSO4), filtered, and concentrated in vacuo. The crude was purified by flash chromatography on silica gel using 1.2% MeOH:CH2Cl2 to provide 5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridine (1.4 g, 89% yield).

후처리

  1. customthe reaction was quenched with saturated aqueous NaHCO3
  2. extractionextracted into CH2Cl2
  3. dry with materialThe combined organic fractions were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by flash chromatography on silica gel using 1.2% MeOH

출처 및 근거

ORD 기록
ord-caf901fffa5c41b7bf32157188433bdc
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08758830B2

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