HCID 118432106, compound → HCID 118431821, compound

HRID 2207911Notes

Reaction equation

HRID 2207911 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=3[F:19])[N:10]=[C:9]([CH:20]([OH:25])[C:21]([F:24])([F:23])[F:22])[CH2:8]2)=[CH:4][CH:3]=1>ClCCl>[Br:1][C:2]1[S:6][C:5]([CH:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=3[F:19])[N:10]=[C:9]([C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[CH2:8]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 118432106HCID 118432106, compound

Product 1

HCID 118431821HCID 118431821, compoundYield 86.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[5-(5-bromo-thiophen-2-yl)-1-(2,4-difluoro-phenyl)-4,5-dihydro-1H-pyrazol-3-yl]-2,2,2-trifluoro-ethanol (9.9 g, 22.4 mmol) prepared in Step 6 in dichloromethane (100.0 mL), was slowly added DMP (10.5 g, 24.7 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 hour, quenched with a saturated sodium thiosulfate solution, and then extracted with diethyl ether. The extract was washed with a saturated solution of sodium hydrogen carbonate, 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: dichloromethane/n-hexane=2/5) to give 8.5 g of the titled compound as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-a2bb43b3d274405b98a1a79b06434193
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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