Pyridine → ethyl 3-acetyl-1-(5-chloro-2-methylphenyl)-1H-pyrazole-5-carboxylate

HRID 925411Notes

Reaction equation

HRID 925411 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:6][N:5]=1)(=[O:3])[CH3:2].[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH3:24])=[C:19](B(O)O)[CH:20]=1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([C:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:6]([C:17]2[CH:16]=[C:15]([Cl:14])[CH:20]=[CH:19][C:18]=2[CH3:24])[N:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 2773336(5-Chloro-2-methylphenyl)boronic acidHCID 162204305-Acetyl-2H-pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 70873383ethyl 3-acetyl-1-(5-chloro-2-methylphenyl)-1H-pyrazole-5-carboxylateYield 43.8%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 3-acetyl-1H-pyrazole-5-carboxylate (364 mg, 2.0 mmol), (5-chloro-2-methylphenyl)boronic acid (680 mg, 4.0 mmol), copper(II) acetate (571 mg, 3.0 mmol) and pyridine (0.32 mL, 4 mmol) in DCM (10 mL) was stirred at r.t. under an air atmosphere for 48 h. After removal of the insolubles by filtration, the filtrate was washed with water and saturated brine, dried over anhydrous sodium sulfate, concentrated in vacuo and purified by flash chromatography (hexane/AcOEt, 90/10) to obtain ethyl 3-acetyl-1-(5-chloro-2-methylphenyl)-1H-pyrazole-5-carboxylate as a white solid (269 mg, 43%),

Workup

  1. customAfter removal of the insolubles
  2. filtrationby filtration
  3. washthe filtrate was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (hexane/AcOEt, 90/10)

Sources & evidence

ORD record
ord-8ef16a13ab8e48d197f7c9467306f6f1
Source dataset
uspto-grants-2016_03
Patent number
US09284298B2

Reaction notes

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