1,4-Dioxane → HCID 118001326, compound

HRID 628516Notes

Reaction equation

HRID 628516 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13](Br)=[C:12]([CH3:15])[N:11]([CH3:16])[N:10]=2)=[CH:5][C:4]=1[CH3:17].O1CCOC[CH2:19]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]([CH3:19])=[C:12]([CH3:15])[N:11]([CH3:16])[N:10]=2)=[CH:5][C:4]=1[CH3:17]

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 139377Methylboronic AcidHCID 83747840HCID 83747840, compound

Product 1

HCID 118001326HCID 118001326, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-(4-methoxy-3-methyl-phenyl)-4-bromo-1,5-dimethyl-1H-pyrazole (described in Reference Preparation example 64) 1.3 g, 1,4-dioxane 30 ml, water 5 ml, methylboronic acid 1.0 g, 1,1′-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane adducts 0.4 g and potassium phosphate 3.7 g was stirred with heating under reflux for nine 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)-1,4,5-trimethyl-1H-pyrazole 0.6 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for nine 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-39f81ea3039e4d1b99c2027e9601ff81
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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