Triethylamine → N-(1-benzyl-2,3-dihydro-1H-indole-5-yl)-methanesulfonamide

HRID 1359142Notes

Reaction equation

HRID 1359142 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+].C(N(CC)CC)C.[S:31](Cl)([CH3:34])(=[O:33])=[O:32]>O1CCCC1.CO.[C].[Pd].O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][S:31]([CH3:34])(=[O:33])=[O:32])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2723923Ammonium formateHCID 98348711-benzyl-5-nitro-2,3-dihydro-1H-indole

Product 1

HCID 9901016N-(1-benzyl-2,3-dihydro-1H-indole-5-yl)-methanesulfonamideYield 76%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

1-benzyl-5-nitro-2,3-dihydro-1H-indole (100 mg, 0.39 mmol) was dissolved in tetrahydrofuran (1 ml) and methanol (1 ml), and ammonium formate (124mg, 1.96 mmol, 5 equivalent) and palladium carbon (10%) of a catalytic amount were added. Then, the solution was stirred at 40° C. for 10 minutes to complete the reduction. After completing the reaction, the solution was filtered through celite, concentrated under reduced pressure, dissolved again in ethyl acetate (10 ml), washed with water and salt solution, dried over anhydrous magnesium sulfate, concentrated again under reduced pressure and then, dried completely under a high-degree vacuum. Afterward, the obtained residue was dissolved with dichloromethane (2.0 ml), cooled to 0° C., blended with triethylamine (0.055 ml, 0.39 mmol) and mesyl chloride (0.031 ml, 0.40 mmol) and then, stirred at the same temperature for 30 minutes to complete the reaction. After pouring water (2.0 ml) again at room temperature, dichloromethane layer was separated, washed with brine, dried over anhydrous magnesium sulfate, and concentrated. Finally, the residue was purified through flash column chromatography (an eluent:ethyl acetate/n-hexane=1/2, v/v). As a result, the present compound (90 mg, productive yield 76%) was obtained.

Workup

  1. customthe reaction
  2. filtrationthe solution was filtered through celite
  3. concentrationconcentrated under reduced pressure
  4. dissolutiondissolved again in ethyl acetate (10 ml)
  5. washwashed with water and salt solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated again under reduced pressure
  8. customdried completely under a high-degree vacuum
  9. dissolutionAfterward, the obtained residue was dissolved with dichloromethane (2.0 ml)
  10. temperaturecooled to 0° C.
  11. stirringstirred at the same temperature for 30 minutes
  12. customthe reaction
  13. customdichloromethane layer was separated
  14. washwashed with brine
  15. dry with materialdried over anhydrous magnesium sulfate
  16. concentrationconcentrated
  17. customFinally, the residue was purified through flash column chromatography (an eluent
  18. customAs a result, the present compound (90 mg, productive yield 76%) was obtained

Sources & evidence

ORD record
ord-87c383fb1ec24241a0d726e184893ba2
Source dataset
uspto-grants-2003_07
Patent number
US06599929B2

Reaction notes

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