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

HRID 62180

반응식

HRID 62180 반응식
[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]

참가 물질

4

반응물 2

HCID 6569Methyl Ethyl KetoneHCID 121574-Bromophenylhydrazine hydrochloride

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-6878b6057b0849929a124e7e29b63d97
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09446042B2

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