Dimethylformamide → 3-chloro-2-(1H-pyrrol-1-yl)pyridine

HRID 2427049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2427049
[NH:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Cl:6][C:7]1[C:8](S(C)(=O)=O)=[N:9][CH:10]=[CH:11][CH:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[Cl:6][C:7]1[C:8]([N:1]2[CH:5]=[CH:4][CH:3]=[CH:2]2)=[N:9][CH:10]=[CH:11][CH:12]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8027PyrroleHCID 10796Cesium carbonateHCID 134334253-Chloro-2-methanesulfonylpyridine

Produkt 1

HCID 587620843-chloro-2-(1H-pyrrol-1-yl)pyridineAusbeute 63,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 1.0 g of pyrrole, 3.0 g of 3-chloro-2-methanesulfonylpyridine, 6.6 g of cesium carbonate and 10 ml of N,N-dimethylformamide was stirred at 60° C. for 27 hours. After the reaction mixture was allowed to cool to room temperature, water was poured and the mixture was extracted with ethyl acetate two times. The organic layers were combined, washed successively with water and an aqueous saturated sodium chloride solution, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to obtain 1.7 g of 3-chloro-2-(1H-pyrrol-1-yl)pyridine of the formula:

Aufarbeitung

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate two times
  3. washwashed successively with water
  4. dry with materialan aqueous saturated sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-35186345844c44f09b7d072764edf631
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968573B2

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