Dimethylformamide → 2-(3-Bromo-1H-pyrazol-1-yl)-3-chloropyridine

HRID 1674518Notes

Reaction equation

HRID 1674518 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.Cl[C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][N:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[Br:1][C:2]1[CH:6]=[CH:5][N:4]([C:8]2[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 169882,3-DichloropyridineHCID 178419412HCID 178419412, compound

Product 1

HCID 210712782-(3-Bromo-1H-pyrazol-1-yl)-3-chloropyridineYield 68.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 10.7 g of 3-bromo-1H-pyrazole, 11.8 g of 2,3-dichloropyridine, 57.3 g of cesium carbonate and 80 mL of N,N-dimethylformamide was stirred at 100° C. for 8 hours. After cooling to room temperature and adding water, the reaction mixture was extracted twice with methyl tert-butyl ether. The organic layers were combined, washed sequentially with water and a 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 12.9 g of 2-(3-bromo-1H-pyrazol-1-yl)-3-chloropyridine. 2-(3-bromo-1H-pyrazol-1-yl)-3-chloropyridine

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe reaction mixture was extracted twice with methyl tert-butyl ether
  3. washwashed sequentially with water
  4. dry with materiala saturated sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7d31a16c78bd461087afe2034ba36e3e
Source dataset
uspto-grants-2011_08
Patent number
US08003650B2

Reaction notes

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