Potassium Carbonate → HCID 86720519, compound

HRID 1755212Notes

Reaction equation

HRID 1755212 reaction equation
[Br-].[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[F:9].[NH:10]1[CH:14]=[CH:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:11]1.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O.[Cu]I>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:10]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:11]2)=[CH:5][C:4]=1[F:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 53416043HCID 53416043, compoundHCID 178469268HCID 178469268, compound

Product 1

HCID 86720519HCID 86720519, 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 3.00 g of 4-chloro-3-fluorobenzenebromide (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), brine (2×50 mL). The organics was 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 (1.2 g, 50%).

Workup

  1. temperatureAfter the mixture was cooled down to room temperature
  2. washwas washed with water (2×50 mL), brine (2×50 mL)
  3. dry with materialThe organics was 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-13210689dbd243ab9b1ec5b61a2aa604
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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