m-Chloroperbenzoic acid → HCID 118431895, compound

HRID 2208072Notes

Reaction equation

HRID 2208072 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[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([S:25][CH3:26])[CH:20]=3)=[CH:15][C:14]=2[F:27])[CH2:11][C:10]([C:28]([C:34]([F:37])([F:36])[F:35])([C:30]([F:33])([F:32])[F:31])[OH:29])=[N:9]1.ClC1C=CC=C(C(OO)=[O:46])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[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([S:25]([CH3:26])=[O:46])[CH:20]=3)=[CH:15][C:14]=2[F:27])[CH2:11][C:10]([C:28]([C:30]([F:32])([F:31])[F:33])([C:34]([F:36])([F:37])[F:35])[OH:29])=[N:9]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 118431773HCID 118431773, compound

Product 1

HCID 118431895HCID 118431895, compoundYield 14.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-(2-chloro-phenyl)-5-(3-fluoro-3′-methylsulfanyl-biphenyl-4-yl)-3-[di-(trifluoromethyl)-hydroxy-methyl]-4,5-dihydro-1H-pyrazole (31.0 mg, 0.06 mmol) prepared in Example 338 in dichloromethane (2.0 mL), was slowly added meta-chloroperbenzoic acid (77%, 22.8 mg, 0.12 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 hours, 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=2/1, 1/1) to give 5.0 mg of the titled compound as a yellow liquid.

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=2/1, 1/1)

Sources & evidence

ORD record
ord-b36eea74c1d6486d9330c9fbc90f9dad
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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