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

HRID 875222ノート

反応式

HRID 875222 の反応式
[OH:1][N:2]=[C:3]([C:9]1[N:13]([CH3:14])[CH:12]=[N:11][CH:10]=1)[C:4]1[S:5][CH:6]=[CH:7][CH:8]=1.Br[CH2:16][C:17]1[N:22]=[C:21]([N:23]2[C:31](=[O:32])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]2=[O:33])[CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C>[CH3:14][N:13]1[C:9]([C:3](=[N:2][O:1][CH2:16][C:17]2[N:22]=[C:21]([N:23]3[C:24](=[O:33])[C:25]4[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:31]3=[O:32])[CH:20]=[CH:19][CH:18]=2)[C:4]2[S:5][CH:6]=[CH:7][CH:8]=2)=[CH:10][N:11]=[CH:12]1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 112323512-(6-Bromomethyl-pyridin-2-YL)-isoindole-1,3-dioneHCID 86650754N-hydroxy-1-(1-methyl-1H-imidazol-5-yl)-1-(2-thienyl)methanimine

生成物 1

HCID 866507552-{6-[({[(1-methyl-1H-imidazol-5-yl)(2-thienyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione収率 90.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of N-hydroxy-1-(1-methyl-1H-imidazol-5-yl)-1-(2-thienyl)methanimine (4.10 g, 19.8 mmol) and 2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (6.89 g, 21.7 mmol) in acetonitrile (100 mL) were added cesium carbonate (13.5 g, 41.4 mmol) and potassium iodide (328 mg, 1.98 mmol). After stirring at room temperature for 24 h, the reaction mixture was filtered, the insolubles washed with ethyl acetate, and the combined filtrates concentrated in vacuo. Purification on silica gel afforded 2-{6-[({[(1-methyl-1H-imidazol-5-yl)(2-thienyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione [7.91 g, yield 86%; HPLC/MS: m/z=444 (M+H); log P(HCOOH)=1.66].

後処理

  1. filtrationthe reaction mixture was filtered
  2. washthe insolubles washed with ethyl acetate
  3. concentrationthe combined filtrates concentrated in vacuo
  4. customPurification on silica gel

出典と根拠

ORDレコード
ord-2f5cd229ee6b4605bfec946acc29aed5
出典データセット
uspto-grants-2015_03
特許番号
US08981111B2

反応ノート

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