Pyridinium hydrobromide → HCID 23152452, compound

HRID 1012307Notes

Reaction equation

HRID 1012307 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:14][NH:15]2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BrH:24].[NH+]1C=CC=CC=1.S([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[C:1]([NH:5][S:6]([C:9]1[CH:17]=[C:16]2[C:12]([C:13]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:14]([Br:24])[NH:15]2)=[CH:11][CH:10]=1)(=[O:7])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 21226041Pyridinium hydrobromideHCID 23152417HCID 23152417, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 23152452HCID 23152452, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N-tert-butyl-3-cyclohexyl-1H-indole-6-sulfonamide (2.29 g, 6.86 mmol) in chloroform (30 ml) was added pyridinium hydrobromide perbromide (2.40 g, 7.50 mmol) under ice-cooling, and the mixture was stirred under ice-cooling for 30 min. 1M aqueous sodium hydrogen sulfite solution was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. A mixed solvent of hexane:ethyl acetate (5:1) was added to the residue. The precipitated solid was collected by filtration and dried in vacuo to give N-tert-butyl-2-bromo-3-cyclohexyl-1H-indole-6-sulfonamide (2.19 g, yield 78.3%).

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 min
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. additionA mixed solvent of hexane:ethyl acetate (5:1) was added to the residue
  9. filtrationThe precipitated solid was collected by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-dd2d72c0f96342a0befbe245cb34d1d0
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

Loading…