HCID 66676088, 화합물 → 5-tert-butyl-6-nitro-1H-indole

HRID 423780노트

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HRID 423780 반응식
[C:1]([C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([NH:14][C:15]#[C:16][Si](C)(C)C)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>CN(C=O)C.[Cu]I>[C:1]([C:5]1[CH:6]=[C:7]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[NH:14][CH:15]=[CH:16]2)([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 1

HCID 66676088HCID 66676088, 화합물

생성물 1

HCID 574702075-tert-butyl-6-nitro-1H-indole수율 69%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

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온도
135 °C

실험 절차

To a solution of 4-tert-butyl-5-nitro-2-trimethylsilanylethynyl-phenylamine (25 g, 86 mmol) in DMF (100 mL) was added CuI (8.2 g, 43 mmol) under a nitrogen atmosphere. The mixture was heated at 135° C. in a sealed pressure flask overnight, cooled down to room temperature and filtered through a short plug of Celite. The filter cake was washed with EtOAc. The combined filtrate was washed with water, dried over Na2SO4 and concentrated. The crude product was purified by column chromatography (10-20% EtOAc/Hexane) to provide 5-tert-butyl-6-nitro-1H-indole as a yellow solid (12.9 g, 69%).

후처리

  1. temperaturecooled down to room temperature
  2. filtrationfiltered through a short plug of Celite
  3. washThe filter cake was washed with EtOAc
  4. washThe combined filtrate was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (10-20% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-10957c97d16e40c8973095c11275b8c7
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101767B2

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