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4-Toluenesulfonyl chloride → 4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 522198
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 522198
[Cl:1][C:2]1[CH:10]=[CH:9][N:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:10]=[CH:9][N:8]=[C:7]2[N:6]([S:17]([C:14]3[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=3)(=[O:19])=[O:18])[CH:5]=[CH:4][C:3]=12
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Komponenten

7

Edukt 4

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 11433187Bis(tetrabutylammonium) sulphate

Produkt 1

HCID 81672684-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a suspension of 4-chloro-7-azaindole (2.32 g, 15.2 mmol) and p-toluenesulfonyl chloride (3.04 g, 15.96 mmol) in toluene (60 mL) and tetrabutylammonium sulfate (0.175 mL, 0.152 mmol, 50% solution in water) was added a solution of sodium hydroxide (0.913 g, 22.8 mmol) in water (36 mL). The biphasic mixture was stirred vigorously overnight, and was partitioned between ethyl acetate and brine. The aqueous layer was separated and extracted with ethyl acetate. The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (Teledyne CombiFlash Rf, 0-20% ethyl acetate in hexane) to provide the title compound. MS (DCI/NH3) m/z 307 (M+H)+.

Aufarbeitung

  1. customwas partitioned between ethyl acetate and brine
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (Teledyne CombiFlash Rf, 0-20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-5070fa44802b47049eb519cd13833671
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09328112B2

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