Hydrochloric Acid → N-(1-benzyl-1H-indole-5-yl)-methanesulfonamide

HRID 1359138Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1359138
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+].[S:24](Cl)([CH3:27])(=[O:26])=[O:25].C(N(CC)CC)C.Cl>O1CCCC1.CO.[Pd]>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2723923Ammonium formateHCID 98563511-Benzyl-5-nitro-1H-indole

Produkt 1

HCID 9944156N-(1-benzyl-1H-indole-5-yl)-methanesulfonamideAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

1-benzyl-5-nitro-1H-indole (50 mg, 0.19 mmol) was dissolved in tetrahydrofuran (1 ml) and methanol (1 ml), and ammonium formate of an excess amount and palladium/carbon (10%) of a catalytic amount were added. The solution was stirred at around 30° C. for 30 minutes to complete the reduction, filtrated through celite, concentrated under reduced pressure, dissolved again in dichloromethane (10 ml), and then washed with water and brine. After drying the resulting solution over anhydrous magnesium sulfate, dichloromethane solution containing amine compound (1-benzyl-5-amino-1H-indole) was obtained. Mesyl chloride (0.015 ml, 0.19 mmol) and triethylamine (0.028 ml, 0.20 mmol) were added to the above obtained solution and stirred at room temperature for 2 hours to complete the reaction. After adding 2N-hydrochloric acid solution (10 ml) to separate layers, dichloromethane solution was induced, washed by using water and brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and then triturated with isooctane and isopropyleter. As a result, the present compound (34mg, productive yield 34%) was obtained as a solid.

Aufarbeitung

  1. filtrationfiltrated through celite
  2. concentrationconcentrated under reduced pressure
  3. dissolutiondissolved again in dichloromethane (10 ml)
  4. washwashed with water and brine
  5. dry with materialAfter drying the resulting solution over anhydrous magnesium sulfate, dichloromethane solution
  6. additioncontaining amine compound (1-benzyl-5-amino-1H-indole)
  7. customwas obtained
  8. stirringstirred at room temperature for 2 hours
  9. customthe reaction
  10. customto separate layers, dichloromethane solution
  11. washwashed
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customtriturated with isooctane and isopropyleter
  15. customAs a result, the present compound (34mg, productive yield 34%) was obtained as a solid

Quellen und Nachweise

ORD-Eintrag
ord-5d66e3a4745b49dc9d554538dcbcda0d
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599929B2

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