Water → HCID 39248127, compound

HRID 337337Notes

Reaction equation

HRID 337337 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1B(O)O.[CH3:14][C:15]1[CH:19]=[C:18]([CH3:20])[NH:17][N:16]=1.N1C=CC=CC=1.O>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[N:16]1[C:15]([CH3:14])=[CH:19][C:18]([CH3:20])=[N:17]1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 62103,5-DimethylpyrazoleHCID 27343412,4-Dimethoxybenzeneboronic acid

Product 1

HCID 39248127HCID 39248127, compoundYield 10.5%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

610.2 mg of 2,4-dimethoxyphenylboronic acid was dissolved in 6 ml of methylene chloride, to the mixture were added 387 mg of 3,5-dimethylpyrazol, 730 mg of copper(II) acetate and 948 μl of pyridine, and the mixture was stirred overnight at room temperature. To the reaction mixture was added 60 ml of water and extracted with 60 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and purified by silica gel column chromatography (hexane:ethyl acetate=3:2) to yield 81.7 mg of the title compound.

Workup

  1. extractionextracted with 60 ml of ethyl acetate
  2. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. custompurified by silica gel column chromatography (hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-b96e35a835ed4e14882dcc79209c8a5e
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Reaction notes

Loading…