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

HRID 404592노트

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HRID 404592 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 68.7%

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-trimethylsilanylethynylphenylamine (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 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).

후처리

  1. temperaturecooled down to room temperature
  2. filtrationfiltered through 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-59e7625e977d4281bb8077700a5bdfc1
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748612B2

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