HCID 67002857, compound → HCID 86761685, compound

HRID 1879669Notes

Reaction equation

HRID 1879669 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[CH2:20][OH:21]>C(Cl)CCl.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12]2)(=[O:9])=[O:10])=[CH:4][C:3]=1[CH:20]=[O:21]

Participants

4

Reactant 1

HCID 67002857HCID 67002857, compound

Product 1

HCID 86761685HCID 86761685, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a solution of [2-Bromo-5-(indole-1-sulfonyl) phenyl] methanol (4.73 grams, 12.92 mmol) (obtained from preparation 2) in ethylene dichloride (75 mL) was added manganese dioxide (8.92 grams, 102.5 mmol). The reaction mass was heated to reflux temperature and maintained under reflux for 3 hours while monitoring the progress of the reaction by TLC. After completion of the reaction, the reaction mass was filtered through hyflow bed and the bed was washed with ethylene dichloride (2×10 mL). The clear filtrate was concentrated under reduced pressure to obtain technical product. The technical material was triturated with of n-hexane (2×15 mL), decanted the solvent and dried under reduced pressure to obtain 3.42 grams title product.

Workup

  1. temperatureThe reaction mass was heated
  2. temperatureto reflux temperature
  3. temperaturemaintained
  4. temperatureunder reflux for 3 hours
  5. customthe progress of the reaction by TLC
  6. customAfter completion of the reaction
  7. filtrationthe reaction mass was filtered through hyflow bed
  8. washthe bed was washed with ethylene dichloride (2×10 mL)
  9. concentrationThe clear filtrate was concentrated under reduced pressure
  10. customto obtain technical product
  11. customThe technical material was triturated with of n-hexane (2×15 mL)
  12. customdecanted the solvent
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-1be05efb93114275865891872c4d8292
Source dataset
uspto-grants-2012_11
Patent number
US08318725B2

Reaction notes

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