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

HRID 2427049Notes

Reaction equation

HRID 2427049 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 587620843-chloro-2-(1H-pyrrol-1-yl)pyridineYield 63.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

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:

Workup

  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

Sources & evidence

ORD record
ord-35186345844c44f09b7d072764edf631
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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