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

HRID 1034653
ノート
印刷プレビュー

反応式

HRID 1034653 の反応式
[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-]>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
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

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

生成物 1

HCID 534129535-Chloro-4-fluoro-1H-pyrrolo[2,3-B]pyridine収率 89.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

5-Chloro-4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (3.0 g, 9.18 mmol) was placed in THF (15 mL) at 0° C. TBAF (10.094 mL, 10.094 mmol) was added dropwise and stirred for 30 minutes. The reaction was then quenched with saturated aqueous NaHCO3 and extracted into DCM. The combined organic fractions were dried, filtered, and concentrated to give the crude product that was purified by column chromatography (500:6 DCM:MeOH) to give 5-chloro-4-fluoro-1H-pyrrolo[2,3-b]pyridine (1.4 g, 89% yield).

後処理

  1. customThe reaction was then quenched with saturated aqueous NaHCO3
  2. extractionextracted into DCM
  3. customThe combined organic fractions were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product that
  7. customwas purified by column chromatography (500:6 DCM:MeOH)

出典と根拠

ORDレコード
ord-cdd08eb2a44e48aca05dc000807508df
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08545897B2

反応ノート

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