Sodium Carbonate → HCID 82112491, compound

HRID 628507Notes

Reaction equation

HRID 628507 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][C:4]=1[CH3:12].Br[C:14]1[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].O1CCOCC1>O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:14]2[CH:15]=[N:16][N:17]([CH3:19])[CH:18]=2)=[CH:5][C:4]=1[CH3:12]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 1674331H-Pyrazole, 4-bromo-1-methyl-HCID 2773487(4-Methoxy-3-methylphenyl)boronic acid

Product 1

HCID 82112491HCID 82112491, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen atmosphere, a mixture of 4-methoxy-3-methyl-phenylboronic acid 1.62 g, 4-bromo-1-methyl-1H-pyrazole 1.57 g, 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex 0.79 g, sodium carbonate 3.51 g, dioxane 100 ml and water 30 ml was stirred with heating under reflux for four hours. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, and was dried over anhydrous magnesium sulfate and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 4-(4-methoxy-3-methyl-phenyl)-1-methyl-1H-pyrazole 1.3 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for four hours
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-4df11527a8e14ee48ff31dca7be012ed
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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