Ethyl acetate hexane → HCID 86613171, compound

HRID 746779Notes

Reaction equation

HRID 746779 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[C:11](C(O)=O)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.CCOC(C)=O.CCCCCC>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([NH:13][S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:11][CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 69251381HCID 69251381, compound

Product 1

HCID 86613171HCID 86613171, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Conditions

Temperature
180 °C

Procedure

Dissolve 1-(4-Bromo-phenyl)-5-(propane-2-sulfonylamino)-1H-pyrazole-4-carboxylic acid (1.952 g, 5.03 mmol) in quinoline (2.79 mL) in a sealed tube. Add copper (0.16 g, 2.51 mmol) and immerse into a pre-heated (180° C.) oil bath and stir for 15 min. Cool to room temperature and remove the solvent under reduced pressure. Dilute with dichloromethane, wash with 1.0M HCl (2×50 mL), dry over sodium sulfate, filter, and concentrate to yield a residue. Subject to silica gel flash column chromatography (15-55% EtOAc/n-hexane) to yield the title compound (1.323 g, 76%).

Workup

  1. temperatureCool to room temperature
  2. customremove the solvent under reduced pressure
  3. additionDilute with dichloromethane
  4. washwash with 1.0M HCl (2×50 mL)
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto yield a residue

Sources & evidence

ORD record
ord-b3ecb18109cc44c68d56b66ea2ca0637
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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