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

HRID 2269573

Reaction equation

HRID 2269573 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

HCID 153373972-(4-Fluorophenyl)-3-(4-(methylsulfonyl)phenyl)indoleYield 53.6%

Reagents, catalysts & solvents 3

HCID 6395Methanesulfonic AcidCatalystHCID 8857Ethyl AcetateSolventHCID 18331056Acetic acid tolueneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-db2bd42e56254025ae9f901673442162
Source dataset
uspto-grants-2001_12
Patent number
US06329421B1

Linked notes

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