1,4-Dioxane → HCID 118236505, compound

HRID 628512Notes

Reaction equation

HRID 628512 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13](Br)=[CH:12][N:11]([CH3:15])[N:10]=2)=[CH:5][C:4]=1[CH3:16].O1CCOC[CH2:18]1.CB(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([CH3:18])=[CH:12][N:11]([CH3:15])[N:10]=2)=[CH:5][C:4]=1[CH3:16]

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 139377Methylboronic AcidHCID 83745857HCID 83745857, compound

Product 1

HCID 118236505HCID 118236505, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-(4-methoxy-3-methyl-phenyl)-4-bromo-1-methyl-1H-pyrazole (described in Reference Preparation example 55) 3.9 g, 1,4-dioxane 80 ml, water 20 ml, methylboronic acid 3.3 g, 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane adducts 1.4 g and potassium phosphate 11.8 g was stirred with heating under reflux for six hours. The reaction 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 3-(4-methoxy-3-methyl-phenyl)-1,4-dimethyl-1H-pyrazole 2.4 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for six hours
  3. extractionThe reaction 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-d591bd0cb94f4b3f868a7049544ca9ef
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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