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

HRID 1092894
ノート
印刷プレビュー

反応式

HRID 1092894 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

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%)

後処理

  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)

出典と根拠

ORDレコード
ord-39de142f40cc4c6e862d3c1c2baab195
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08129544B2

反応ノート

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