Phenylhydrazine → 2-(4-Fluorophenyl)-3-(4-(methylsulfonyl)phenyl)indole

HRID 441158

Reaktionsgleichung

Reaktionsgleichung von HRID 441158
[C:1]1([NH:7]N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](=O)[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[CH:12][CH:11]=1>C1(C)C=CC=CC=1.CC(O)=O.CS(O)(=O)=O.CCOC(C)=O>[F:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[NH:7][C:1]3[C:6]([C:17]=2[C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=2)=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:14][CH:15]=1

Komponenten

6

Edukt 2

HCID 7516PhenylhydrazineHCID 112433011-(4-Fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone

Produkt 1

HCID 153373972-(4-Fluorophenyl)-3-(4-(methylsulfonyl)phenyl)indoleAusbeute 53,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6395Methanesulfonic AcidKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 18331056Acetic acid tolueneLösungsmittel

Versuchsvorschrift

A solution of phenylhydrazine (203 uL, 1.73 mmol) and 1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone (510 mg, 1.73 mmol) (Step 2) in a mixture of toluene/HOAc (2:1; 5 mL) containing 1 drop of methanesulfonic acid was stirred at r.t. overnight. The reaction mixture was diluted with EtOAc and was washed successively with H2O, 1M NaOH, H2O and dried. Evaporation of the solvent gave a residue which was purified by silica gel chromatography using EtOAc/hexane (1:3+10% CH2Cl2) as eluent to afford 339 mg of the title compound.

Aufarbeitung

  1. washwas washed successively with H2O, 1M NaOH, H2O
  2. customdried
  3. customEvaporation of the solvent
  4. customgave a residue which
  5. customwas purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-22ddc8ef9154428ab43d282339883e10
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05521213

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