Potassium Iodide → 2-(6-{[({[3-(dimethylamino)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione

HRID 452564ノート

反応式

HRID 452564 の反応式
[OH:1][N:2]=[C:3]([C:13]1[N:17]([CH3:18])[N:16]=[N:15][N:14]=1)[C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[N:7]([CH3:9])[CH3:8].Br[CH2:20][C:21]1[N:26]=[C:25]([N:27]2[C:35](=[O:36])[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]2=[O:37])[CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C>[CH3:8][N:7]([CH3:9])[C:6]1[CH:5]=[C:4]([C:3](=[N:2][O:1][CH2:20][C:21]2[N:26]=[C:25]([N:27]3[C:28](=[O:37])[C:29]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:35]3=[O:36])[CH:24]=[CH:23][CH:22]=2)[C:13]2[N:17]([CH3:18])[N:16]=[N:15][N:14]=2)[CH:12]=[CH:11][CH:10]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 112323512-(6-Bromomethyl-pyridin-2-YL)-isoindole-1,3-dioneHCID 1363527053-[(hydroxyimino)(1-methyl-1H-tetrazol-5-yl)methyl]-N,N-dimethylaniline

生成物 1

HCID 866531502-(6-{[({[3-(dimethylamino)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione収率 97%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a stirred solution of 3-[(hydroxyimino)(1-methyl-1H-tetrazol-5-yl)methyl]-N,N-dimethylaniline (2.90 g, 11 mmol) in dry acetonitrile (100 mL) were added 2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (3.74 g, 11.8 mmol), cesium carbonate (7.33 g, 22.5 mmol) and potassium iodide (0.89 g, 5.36 mmol). The reaction mixture was stirred at room temperature for 24 h, then insolubles were removed by filtration and washed with dichloromethane. The filtrates were combined and concentrated in vacuo. The residue was dissolved in dichloromethane (500 mL), washed with water (2×200 mL), and the organic layer was dried over MgSO4 and concentrated in vacuo to afford 2-(6-{[({[3-(dimethylamino)phenyl](1-methyl-1H-tetrazol-5-yl)methylene}amino)oxy]methyl}pyridin-2-yl)-1H-isoindole-1,3(2H)-dione as an orange solid [5.28 g, yield 97%; HPLC/MS:m/z=483 (M+H); log P(HCOOH)=3.17].

後処理

  1. custominsolubles were removed by filtration
  2. washwashed with dichloromethane
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane (500 mL)
  5. washwashed with water (2×200 mL)
  6. dry with materialthe organic layer was dried over MgSO4
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f97c8cd697b34f3abd42e444e8b70a8a
出典データセット
uspto-grants-2013_07
特許番号
US08492388B2

反応ノート

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