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

HRID 441158

反応式

HRID 441158 の反応式
[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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6395Methanesulfonic Acid触媒HCID 8857Ethyl Acetate溶媒HCID 18331056Acetic acid toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-22ddc8ef9154428ab43d282339883e10
出典データセット
uspto-grants-1996_05
特許番号
US05521213

関連ノート

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