HCID 23152482, compound → HCID 23152417, compound

HRID 1012306Notes

Reaction equation

HRID 1012306 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][CH:20]=[CH:19]3)=[CH:14][NH:15]2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[OH-].[Pd+2]>[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:7])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 23152482HCID 23152482, compound

Product 1

HCID 23152417HCID 23152417, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A suspension of N-tert-butyl-3-(2-cyclohexen-1-yl)-1H-indole-6-sulfonamide (2.82 g, 8.48 mmol) and 20% palladium hydroxide/carbon (300 mg) in methanol (30 ml) was stirred at room temperature for 4 hr under a hydrogen atmosphere of 1 atm. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. Hexane was added to the residue. The precipitated solid was collected by filtration and dried in vacuo to give N-tert-butyl-3-cyclohexyl-1H-indole-6-sulfonamide (2.29 g, yield 82.0%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionHexane was added to the residue
  4. filtrationThe precipitated solid was collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-7c0a2ca1f98143918e804c1cf4cda538
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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