Isopropanol → N-(3-Methyl-1H-indole-7-yl)-4-(methylsulfonyl)benzenesulfonamide

HRID 1173106Notes

Reaction equation

HRID 1173106 reaction equation
[BH4-].[Na+].CC(O)C.[CH:7]([C:9]1[C:17]2[C:12](=[C:13]([N+:18]([O-])=O)[CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)=O.[CH3:21][S:22]([C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1)(=[O:24])=[O:23]>[C].[Pd].O>[CH3:7][C:9]1[C:17]2[C:12](=[C:13]([NH:18][S:31]([C:28]3[CH:27]=[CH:26][C:25]([S:22]([CH3:21])(=[O:24])=[O:23])=[CH:30][CH:29]=3)(=[O:33])=[O:32])[CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 27351824-Methanesulfonylbenzene-1-sulfonyl chlorideHCID 27624387-nitro-1H-indole-3-carbaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 22228584N-(3-Methyl-1H-indole-7-yl)-4-(methylsulfonyl)benzenesulfonamideYield 61%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

580 mg (15.3 mmol) of sodium borohydride and 150 mg of 10% palladium-carbon were added to a 2-propanol suspension (25 ml) containing 300 mg (1.58 mmol) of 3-formyl-7-nitro-1H-indole, followed by refluxing for 6 hours. After water was added to the reaction system, the catalyst was filtered off. The filtrate was extracted with ethyl acetate, and the extract was washed with brine and then dried over magnesium sulfate. The solvent was evaporated, and the residue was dissolved in 5 ml of pyridine. The mixture was reacted and treated with 170 mg (0.67 mmol) of 4-(methylsulfonyl)benzenesulfonyl chloride in the same manner as in Example 1a, to give 149 mg of the title compound.

Workup

  1. temperatureby refluxing for 6 hours
  2. filtrationthe catalyst was filtered off
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washthe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. dissolutionthe residue was dissolved in 5 ml of pyridine
  8. customThe mixture was reacted

Sources & evidence

ORD record
ord-0100aac452864740bef4442add621a39
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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