Cesium carbonate → HCID 58063460, compound

HRID 474332Notes

Reaction equation

HRID 474332 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:18])=[C:6]([C:8]2[NH:12][N:11]=[CH:10][C:9]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][CH2:27][O:28][CH3:29]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:18])=[C:6]([C:8]2[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][N:11]([CH2:26][CH2:27][O:28][CH3:29])[N:12]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 58063168HCID 58063168, compound

Product 1

HCID 58063460HCID 58063460, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 5-(5-chloro-2-methylphenyl)-1H-pyrazole-4-carboxylate (0.2286 g, 0.8636 mmol), cesium carbonate (359.1 mg, 1.102 mmol, 1.276 equiv) and 1-bromo-2-methoxyethane in N,N-dimethylformamide (6 mL) was heated at 50° C. After 2.5 hours, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate, filtered, and concentrated to yield 257.7 mg (92%) of ethyl 3-(5-chloro-2-methylphenyl)-1-(2-methoxyethyl)-1H-pyrazole-4-carboxylate, which was carried forward without purification. LCMS (ESI) m+H=323.2.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-961c8d15b6524c81a98ee85d177dd145
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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