Dichloromethane → 1-(Phenylsulfonyl)-1H-indole

HRID 450835

Reaktionsgleichung

Reaktionsgleichung von HRID 450835
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1C(OCC)=O.[H-].[Na+].[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.ClCCl>CN(C=O)C.O>[C:17]1([S:23]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 73125Ethyl indole-2-carboxylate

Produkt 1

HCID 3150171-(Phenylsulfonyl)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred and cooled (to about 0° C.) solution of ethyl indole-2-carboxylate 10 (1 eq.) in DMF (2 ml/mmol) under N2, was added NaH (60% in oil, 1.2 eq.) portionwise. When gas evolution stopped, benzenesulfonyl chloride (1.2 eq.) was added. The reaction mixture was stirred for about 1 hour (TLC monitoring, eluent dichloromethane); a small amount of water then was added carefully and the DMF was evaporated. The crude residue was dissolved in ethyl acetate and washed with water and brine. After drying and evaporation of the solvents, the compound was purified by chromatography on silica gel (eluent: C6H12/EtOAc 9/1 to 7/3) to give the N-phenylsulfonylindole 62c.

Aufarbeitung

  1. customthe DMF was evaporated
  2. dissolutionThe crude residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. customAfter drying
  5. customevaporation of the solvents
  6. customthe compound was purified by chromatography on silica gel (eluent: C6H12/EtOAc 9/1 to 7/3)

Quellen und Nachweise

ORD-Eintrag
ord-6a32503dd37d421f8a901bbb005763f0
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486991B2

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