Hydrochloric Acid → HCID 66820740, compound

HRID 577158Notes

Reaction equation

HRID 577158 reaction equation
Br[C:2]1[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4][N:5]([CH2:7][CH3:8])[CH:6]=1.[CH2:13]([Zn]CC)[CH3:14].O.Cl>O1CCOCC1>[CH2:7]([N:5]1[CH:6]=[C:2]([CH2:13][CH3:14])[C:3]([C:9]([O:11][CH3:12])=[O:10])=[N:4]1)[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7017643Methyl 4-bromo-1-ethyl-1H-pyrazole-3-carboxylateHCID 178418750HCID 178418750, compound

Product 1

HCID 66820740HCID 66820740, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

Methyl 4-bromo-1-ethyl-1H-pyrazole-3-carboxylate (2.5 g, 11.4 mmol) was dissolved in anhydrous dioxane (90 mL). A solution of diethyl zinc (10.4 mL, 11.4 mmol, 1.1 M in toluene) was added dropwise, and then was added (1,1′-bis(diphenylphosphino)ferrocene)dichloropalladium (125 mg, 171 μmol). The mixture was heated at 75° C. overnight, and water plus 1 N HCl were added. The mixture was extracted 3 times with ethyl acetate, and the combined organic phases were washed with brine and dried over sodium sulfate. After evaporation, the residue was dissolved in DCM and purified on silica gel using 0-30% hexane/ethyl acetate to afford methyl 1,4-diethyl-1H-pyrazole-3-carboxylate (912 mg, 48% yield).

Workup

  1. extractionThe mixture was extracted 3 times with ethyl acetate
  2. washthe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customAfter evaporation
  5. dissolutionthe residue was dissolved in DCM
  6. custompurified on silica gel using 0-30% hexane/ethyl acetate

Sources & evidence

ORD record
ord-a399fe10770a4ad492579251f67c4c43
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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