Sodium Iodide → 1-(4-{[tert-Butyl(dimethyl)silyl]oxy}butyl)-7-methoxyquinoxalin-2(1H)-one

HRID 1846989ノート

反応式

HRID 1846989 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1.[H-].[Li+].Br[CH2:17][CH2:18][CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[Si:22]([O:21][CH2:20][CH2:19][CH2:18][CH2:17][N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[N:7]=[CH:8][C:9]1=[O:13])([C:25]([CH3:26])([CH3:27])[CH3:28])([CH3:23])[CH3:24]

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 62714Lithium hydrideHCID 4913197-Methoxy-1,2-dihydroquinoxalin-2-oneHCID 582370(4-Bromobutoxy)(tert-butyl)dimethylsilane

生成物 1

HCID 867249211-(4-{[tert-Butyl(dimethyl)silyl]oxy}butyl)-7-methoxyquinoxalin-2(1H)-one収率 44%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

7-Methoxyquinoxalin-2(1H)-one (synthesized with reference to WO2009/1126; 400 mg, 2.27 mmol) was dissolved in N,N-dimethylformamide (8 ml). The solution was cooled in an ice bath, lithium hydride (purity 90%, 26 mg, 2.95 mmol) was then added thereto and the mixture was stirred at room temperature for 40 minutes. The reaction solution was cooled in an ice bath again, (4-bromobutoxy)(tert-butyl)dimethylsilane (synthesized with reference to Journal of Medicinal Chemistry, 2008, vol. 51, No. 18, pages 5690-5701; 580 mg, 2.17 mmol) and sodium iodide (442 mg, 2.95 mmol) were added thereto, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, washed sequentially with saturated sodium chloride solution (×2), water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to yield 363 mg (44%) of the title compound in the form of a light yellow syrup.

後処理

  1. temperatureThe solution was cooled in an ice bath
  2. temperatureThe reaction solution was cooled in an ice bath again
  3. stirringthe mixture was stirred overnight at room temperature
  4. washwashed sequentially with saturated sodium chloride solution (×2), water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-a65b27a00fa847dbb78d98e7de41bb4a
出典データセット
uspto-grants-2015_02
特許番号
US08952010B2

反応ノート

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