(Trifluoromethyl)trimethylsilane → HCID 67545637、化合物

HRID 2386786ノート

反応式

HRID 2386786 の反応式
O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:22][C:23]([Si](C)(C)C)([F:25])[F:24].[Br:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37]([CH3:52])[C:38]([C:40]2[CH:51]=[CH:50][C:43]3[N:44]([CH3:49])[C:45](=[O:48])[N:46]([CH3:47])[C:42]=3[CH:41]=2)=[O:39])=[C:33]([Cl:53])[CH:32]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O.CO>[Br:30][C:31]1[CH:36]=[CH:35][C:34]([CH:37]([CH3:52])[C:38]([C:40]2[CH:51]=[CH:50][C:43]3[N:44]([CH3:49])[C:45](=[O:48])[N:46]([CH3:47])[C:42]=3[CH:41]=2)([OH:39])[C:23]([F:25])([F:24])[F:22])=[C:33]([Cl:53])[CH:32]=1

参加物

8

反応物 4

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 66697339HCID 66697339、化合物

生成物 1

HCID 67545637HCID 67545637、化合物

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

Tetrabutylammonium fluoride trihydrate (31 mg) was added to a solution of (trifluoromethyl)trimethylsilane (1 ml of a 2M solution in THF) and 5-[2-(4-bromo-2-chloro-phenyl)-propionyl]-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one (410 mg) in THF (20 ml) at room temperature. The mixture was stirred for 30 min at room temperature. MeOH (1 ml) and 1M tetrabutylammonium fluoride in THF (1 ml) were added and the mixture was stirred 1 h at room temperature. Water (50 ml) was added and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated to an oil. The residue was purified by flash chromatography (SiO2, 0 to 100% EtOAc/heptane) to give the title compound (400 mg) as a colorless oil. MS (m/e)=479.0 [M+H+].

後処理

  1. stirringthe mixture was stirred 1 h at room temperature
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated to an oil
  5. customThe residue was purified by flash chromatography (SiO2, 0 to 100% EtOAc/heptane)

出典と根拠

ORDレコード
ord-3260e3189fca40208ba220e733c64891
出典データセット
uspto-grants-2012_09
特許番号
US08268820B2

反応ノート

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