Methyl Ethyl Ketone → 5-Bromo-2,3-dimethyl-1H-indole

HRID 508244ノート

反応式

HRID 508244 の反応式
[CH3:1][C:2](=O)[CH2:3][CH3:4].Cl.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14]N)=[CH:10][CH:9]=1>CCO>[Br:7][C:8]1[CH:13]=[C:12]2[C:11](=[CH:10][CH:9]=1)[NH:14][C:3]([CH3:4])=[C:2]2[CH3:1]

参加物

4

反応物 2

HCID 6569Methyl Ethyl KetoneHCID 121574-Bromophenylhydrazine hydrochloride

生成物 1

HCID 127930975-Bromo-2,3-dimethyl-1H-indole収率 67%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Following a published procedure (Gundersen, E. G. U.S. Patent App. Publ. US 2005/070592) 2-Butanone (0.11 mL, 1.278 mmol) was added to a solution of 4-bromophenylhydrazine hydrochloride (0.300 g, 1.342 mmol in EtOH (3.8 mL). The mixture was heated to reflux for 22 h, concentrated in vacuo, and partitioned between EtOAc and 1N HCl. The organic layer was washed with H2O and saturated aqueous NaHCO3, dried over Na2SO4, filtered, and concentrated. The crude residue was purified by chromatography (SiO2, 0-20% EtOAc/Hexane) to afford the desired indole as a pink powder (200 mg, 67%).

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 22 h
  3. concentrationconcentrated in vacuo
  4. custompartitioned between EtOAc and 1N HCl
  5. washThe organic layer was washed with H2O and saturated aqueous NaHCO3
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was purified by chromatography (SiO2, 0-20% EtOAc/Hexane)

出典と根拠

ORDレコード
ord-7ec1b5d3dbfc478b937ba3b3ce5864c6
出典データセット
uspto-grants-2015_08
特許番号
US09095571B2

反応ノート

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