2-Chloropyridine → Ethyl 1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate

HRID 1260330Notes

Reaction equation

HRID 1260330 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][NH:9][CH:10]=1)=[O:5])[CH3:2].Cl[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CCCCCCC.C(OCC)(=O)C>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 79772-ChloropyridineHCID 10796Cesium carbonateHCID 142179ethyl 1H-pyrazole-4-carboxylateHCID 21899848Ethylacetate heptane

Product 1

HCID 15192741Ethyl 1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1H-pyrazol-4-carboxylic acid ethyl ester (1.25 g, 8.9 mmol), 2-chloropyridine (2.02 g, 17.8 mmol) and cesium carbonate (8.7 g, 26.75 mmol) in DMF (26.8 ml) was irradiated under microwave conditions at 180° C. for 10 min. The reaction mixture was extracted with diethylether, and the combined organic phases were washed with water and brine. The product was obtained after silica gel chromatography using a heptane/ethyl acetate gradient as white solid (0.81 mg, 42%). MS: M=218.2 (M+H)+

Workup

  1. extractionThe reaction mixture was extracted with diethylether
  2. washthe combined organic phases were washed with water and brine
  3. customThe product was obtained after silica gel chromatography

Sources & evidence

ORD record
ord-5c5dde47666c4cc4a7d363076218f1cb
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

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