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Sodium Iodide → 2-Bromo-1-[3-(t-butyldimethylsilanyloxy)-2-(tetrahydropyran-2-yloxy)propyl]-4-nitroimidazole

HRID 2221418
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HRID 2221418 반응식
[Br:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[Si:10]([O:17][CH2:18][CH:19]([O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)[CH2:20]Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[Br:1][C:2]1[N:3]([CH2:20][CH:19]([O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[CH2:18][O:17][Si:10]([C:13]([CH3:16])([CH3:14])[CH3:15])([CH3:12])[CH3:11])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1
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참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 477542-Bromo-4-nitroimidazoleHCID 230802371-(t-Butyldimethylsilanyloxy)-3-chloro-2-(tetrahydropyran-2-yloxy)propane

생성물 1

HCID 230802502-Bromo-1-[3-(t-butyldimethylsilanyloxy)-2-(tetrahydropyran-2-yloxy)propyl]-4-nitroimidazole수율 70.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
110 °C

실험 절차

2-Bromo-4-nitroimidazole (7.63 g) and 1-(tert-butyldimethylsilanyloxy)-3-chloro-2-(tetrahydropyran-2-yloxy)propane (12 g) were dissolved in N,N-dimethylformamide (80 ml), then potassium carbonate (6.6 g) and sodium iodide (6.3 g) were added thereto, and the reaction mixture was heated and stirred at 110° C. for 12 hours. Ice-water (240 ml) was added, extracted twice with ethyl acetate (150 ml), and the extracts were combined together and washed with an aqueous solution being saturated with sodium chloride (100 ml), then dried over anhydrous magnesium sulfate. After being filtrated under a reduced pressure, the filtrate was concentrated under a reduced pressure. The residue obtained was purified by use of a silica gel column chromatography (eluent: dichloromethane/ethyl acetate=100/1), there was obtained 2-bromo-1-[3-(t-butyldimethylsilanyloxy)-2-(tetrahydropyran-2-yloxy)propyl]-4-nitroimidazole (12.69 g, yield: 68.7%)

후처리

  1. temperaturethe reaction mixture was heated
  2. extractionextracted twice with ethyl acetate (150 ml)
  3. washwashed with an aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter being filtrated under a reduced pressure
  6. concentrationthe filtrate was concentrated under a reduced pressure
  7. customThe residue obtained
  8. customwas purified by use of a silica gel column chromatography (eluent: dichloromethane/ethyl acetate=100/1)

출처 및 근거

ORD 기록
ord-3c13a97aff9d4265a7db2193946190c5
출처 데이터셋
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07368579B2

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