Potassium Carbonate → HCID 14129378, compound

HRID 1755214Notes

Reaction equation

HRID 1755214 reaction equation
[Br-].[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH:9]1[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:10]1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.[Cu]I>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 866640794-ChlorobenzenebromideHCID 178469268HCID 178469268, compound

Product 1

HCID 14129378HCID 14129378, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A 50 mL of flask was charged with 2.87 g of 4-chlorobenzenebromide (15 mmol), 1.40 g of ethyl 1-H-pyrazole-3-carboxylate (10 mmol), 400 mg of CuI (2.0 mmol), 4.5 g of K2CO3 (3.3 mmol) and 0.9 mL of trans-N,N′-dimethylcyclohexayldiamine (2.0 mmol). The resulting mixture was stirred at 140° C. for 3 h. After the mixture was cooled down to room temperature, it was diluted with 200 mL EtOAc and then was washed with water (2×50 mL) and brine (2×50 mL). The organics were dried over MgSO4 and concentrated under reduced pressure. The residued was purified via flash column chromatography on silica gel (0-25% EtOAc in hexanes) to get the desired product (1.25 g, 50%).

Workup

  1. temperatureAfter the mixture was cooled down to room temperature
  2. washwas washed with water (2×50 mL) and brine (2×50 mL)
  3. dry with materialThe organics were dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residued was purified via flash column chromatography on silica gel (0-25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-905f48c402f64c8b98b6d28604c9e167
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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