m-Chloroperbenzoic acid → HCID 118432066, compound

HRID 2208005Notes

Reaction equation

HRID 2208005 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]([C:13]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][CH:20]=3)[CH:16]=[CH:15][CH:14]=2)[CH2:11][C:10]([C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29])=[N:9]1.ClC1C=CC=C(C(OO)=[O:42])C=1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]([C:13]2[N:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:26])=[O:42])=[CH:21][CH:20]=3)[CH:16]=[CH:15][CH:14]=2)[CH2:11][C:10]([C:27]([F:33])([F:32])[C:28]([F:30])([F:31])[F:29])=[N:9]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 118431847HCID 118431847, compound

Product 1

HCID 118432066HCID 118432066, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-(2-chloro-phenyl)-5-[2-(4-methylsulfanyl-phenyl)-pyridin-6-yl]-3-pentafluoroethyl-4,5-dihydro-1H-pyrazole (9.0 mg, 0.02 mmol) prepared in Example 153 in dichloromethane (1.0 mL), was slowly added meta-chloroperbenzoic acid (77%, 2.0 mg, 0.01 mmol) at 0° C. The reaction mixture was stirred at room temperature for 30 minutes, quenched with a saturated solution of sodium hydrogen carbonate, and then extracted with dichloromethane three times. The combined extract was washed with brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=3/1) to give 2.0 mg of the titled compound as a white solid.

Workup

  1. customat 0° C
  2. customquenched with a saturated solution of sodium hydrogen carbonate
  3. extractionextracted with dichloromethane three times
  4. extractionThe combined extract
  5. washwas washed with brine
  6. dry with materialdried on anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give a yellow liquid residue
  9. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=3/1)

Sources & evidence

ORD record
ord-459eb65d7cd3496e99de8d2ec6b24e47
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

Loading…