HCID 23152475, compound → HCID 23152479, compound

HRID 1012304Notes

Reaction equation

HRID 1012304 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/N(C)C)=[C:11]([N+:20]([O-])=O)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.C(O)C.[Pd]>[C:1]([NH:5][S:6]([C:9]1[CH:10]=[C:11]2[C:12]([CH:15]=[CH:16][NH:20]2)=[CH:13][CH:14]=1)(=[O:7])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 1

HCID 23152475HCID 23152475, compound

Product 1

HCID 23152479HCID 23152479, compoundYield 87.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of N-tert-butyl-4-((E)-2-dimethylaminovinyl)-3-nitrobenzenesulfonamide (5.41 g, 16.5 mmol) and 7.5% palladium/carbon (500 mg) in tetrahydrofuran (50 ml) and ethanol (50 ml) was stirred at room temperature for 3.5 hr under a hydrogen atmosphere of 3.5 atm. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was successively washed with 1N hydrochloric acid and saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to give N-tert-butyl-1H-indole-6-sulfonamide (3.62 g, yield 87.1%).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionEthyl acetate was added to the residue
  4. washthe mixture was successively washed with 1N hydrochloric acid and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a131108c3af247bfbd2fe4a545cc370c
Source dataset
uspto-grants-2011_07
Patent number
US07977331B1

Reaction notes

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