Sodium Carbonate → HCID 13370527, compound

HRID 1843092Notes

Reaction equation

HRID 1843092 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4](B2OC(C)(C)C(C)(C)O2)=[N:3]1.Br[C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>O.O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][N:2]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)=[N:3]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 24436Sodium SulfateHCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 67379260Methyl 1-Methyl-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-pyrazole-5-carboxylate

Product 1

HCID 13370527HCID 13370527, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

1.50 g (5.36 mmol) of methyl 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-5-carboxylate (for preparation see WO2007/034278A2), 1.21 g (5.36 mmol) of 1-bromo-4-(trifluoromethyl)benzene and bis(triphenylphosphine)palladium(II) chloride are initially introduced under argon and admixed with 6.69 ml of a 2M solution of sodium carbonate in water and 20 ml of dioxane. The reaction mixture is heated at 100° C. for three hours and, after cooling over Celite and sodium sulphate, is filtered. The filter cake is afterwashed with ethyl acetate and the filtrate is concentrated by evaporation on a rotary evaporator. Chromatographic purification on silica gel gives 529 mg of methyl 1-methyl-3-[4-(trifluoromethyl)phenyl]-1H-pyrazole-5-carboxylate (35%) (for preparation also see DD1984/210265).

Workup

  1. additionare initially introduced under argon
  2. filtrationis filtered
  3. concentrationthe filtrate is concentrated by evaporation on a rotary evaporator
  4. customChromatographic purification on silica gel

Sources & evidence

ORD record
ord-e877db68c98e4a269e0cc349f8f31e2b
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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