Tetrabutylammonium Fluoride → N-[2-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)-1H-indol-6-yl]-N-methylacetamide

HRID 2068884노트

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HRID 2068884 반응식
[CH3:1][C:2]1([CH3:41])[CH2:10][C:9]2[N:8](COCC[Si](C)(C)C)[N:7]=[C:6]([C:19]3[N:20](COCC[Si](C)(C)C)[C:21]4[C:26]([CH:27]=3)=[CH:25][CH:24]=[C:23]([N:28]([CH3:32])[C:29](=[O:31])[CH3:30])[CH:22]=4)[C:5]=2[CH2:4][CH2:3]1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C)C=O>[CH3:1][C:2]1([CH3:41])[CH2:10][C:9]2[NH:8][N:7]=[C:6]([C:19]3[NH:20][C:21]4[C:26]([CH:27]=3)=[CH:25][CH:24]=[C:23]([N:28]([CH3:32])[C:29](=[O:31])[CH3:30])[CH:22]=4)[C:5]=2[CH2:4][CH2:3]1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 58550307N-(2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indol-6-yl)-N-methylacetamide

생성물 1

HCID 136127380N-[2-(6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazol-3-yl)-1H-indol-6-yl]-N-methylacetamide수율 42%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

Under an argon atmosphere, to a solution of N-(2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indol-6-yl)-N-methylamine (100 mg, 0.18 mmol) and triethylamine (75 μl, 0.54 mmol) in chloroform (1.5 ml) was added acetyl chloride (19 μl, 0.27 mmol) at room temperature, and the mixture was stirred for 2 hr. Water was added to the reaction mixture, and the mixture was extracted three times with ethyl acetate. The combined organic layers were washed successively with water and saturated brine, and dried over sodium sulfate. Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to give N-(2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indol-6-yl)-N-methylacetamide. A solution of the obtained N-(2-{6,6-dimethyl-1-[2-(trimethylsilyl)ethoxymethyl]-4,5,6,7-tetrahydro-1H-indazol-3-yl}-1-[2-(trimethylsilyl)ethoxymethyl]-1H-indol-6-yl)-N-methylacetamide in N,N-dimethylformamide (1.4 ml) was added to tetrabutylammonium fluoride (1.8 ml, 1.8 mmol) concentrated in advance under reduced pressure. Ethylenediamine (0.7 ml) was added, and the mixture was stirred with heating at 90° C. for 24 hr. After cooling, water and ethyl acetate were added, and the organic layer was separated. Then, the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed successively with water and saturated brine, and dried over sodium sulfate. Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by thin layer silica gel chromatography to give the title compound (26 mg, yield 42%).

후처리

  1. concentrationconcentrated in advance under reduced pressure
  2. additionEthylenediamine (0.7 ml) was added
  3. temperatureAfter cooling
  4. additionwater and ethyl acetate were added
  5. customthe organic layer was separated
  6. extractionThen, the aqueous layer was extracted twice with ethyl acetate
  7. washThe combined organic layers were washed successively with water and saturated brine
  8. dry with materialdried over sodium sulfate
  9. customSodium sulfate was removed by filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe residue was purified by thin layer silica gel chromatography

출처 및 근거

ORD 기록
ord-c382a9a3de3846a3802f4ad3058473c1
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299070B2

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