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

HRID 441158

반응식

HRID 441158 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 6395Methanesulfonic Acid촉매HCID 8857Ethyl Acetate용매HCID 18331056Acetic acid toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-22ddc8ef9154428ab43d282339883e10
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05521213

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