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

HRID 887696Notes

Reaction equation

HRID 887696 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+].O>CN(C=O)C>[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 962WaterHCID 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 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

The crude product of 3-bromo-1H-pyrazole (10.7 g) was dissolved in DMF (80 mL), 2,3-dichloropyridine (11.8 g) and caesium carbonate (57.3 g) were added and the mixture was stirred for 8 h at 100° C. After addition of water, the mixture was extracted 2× with MTB-ether, the combined org. layers were washed 2× with water, brine, dried over MgSO4 and concentrated in vacuum. The residue was purified by column chromatography (silica gel 60, hexane/ethyl acetate=5:1, Rf=0.20) to afford 12.9 g of the title compound of the formula

Workup

  1. extractionthe mixture was extracted 2× with MTB-ether
  2. washlayers were washed 2× with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by column chromatography (silica gel 60, hexane/ethyl acetate=5:1, Rf=0.20)

Sources & evidence

ORD record
ord-00e39847a6e7459cb15016c6388e7c6d
Source dataset
uspto-grants-2012_08
Patent number
US08247431B2

Reaction notes

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