Potassium Iodide → HCID 44183559, compound

HRID 2386162Notes

Reaction equation

HRID 2386162 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[CH2:10][N:9]=2)=[CH:4][CH:3]=1.[NH:25]1[CH:29]=[N:28][CH:27]=[N:26]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN1CCCC1=O.[Cu](I)I.O>[Cl:24][C:19]1[CH:18]=[C:17]([C:11]2([C:13]([F:16])([F:15])[F:14])[CH2:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([N:25]4[CH:29]=[N:28][CH:27]=[N:26]4)=[CH:3][CH:4]=3)[CH2:12]2)[CH:22]=[C:21]([Cl:23])[CH:20]=1

Participants

8

Reactant 4

HCID 4875Potassium IodideHCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 86648072HCID 86648072, compound

Product 1

HCID 44183559HCID 44183559, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
190 °C

Procedure

To a suspension of 1.60 g of 2-(4-bromophenyl)-4-(3,5-dichlorophenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrole, 0.53 g of 1,2,4-triazole, 1.01 g of potassium carbonate and 1.25 g of potassium iodide in 20 mL of N-methylpyrrolidone, 0.21 g of copper iodide was added and the resultant reaction mixture was stirred at 190° C. for 1 hour. After the completion of the reaction, the reaction mixture was left to be cooled down to room temperature and was poured carefully into 50 mL of water, followed by extracting the reaction mixture with ethyl acetate (30 mL×2). The organic phase was dehydrated and dried over a saturated brine and anhydrous sodium sulfate in this order and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (3:2) to obtain 0.27 g of the objective substance as a white crystal.

Workup

  1. additionwas added
  2. customthe resultant reaction mixture
  3. customAfter the completion of the reaction
  4. waitthe reaction mixture was left
  5. temperatureto be cooled down to room temperature
  6. extractionby extracting the reaction mixture with ethyl acetate (30 mL×2)
  7. dry with materialdried over a saturated brine and anhydrous sodium sulfate in this order
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resultant residue was purified by silica gel column chromatography
  10. washeluting with ethyl acetate-hexane (3:2)
  11. customto obtain 0.27 g of the objective substance as a white crystal

Sources & evidence

ORD record
ord-f61109b8264049a2b81d592372bd5474
Source dataset
uspto-grants-2012_09
Patent number
US08268754B2

Reaction notes

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