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 875222노트

반응식

HRID 875222 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-2f5cd229ee6b4605bfec946acc29aed5
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08981111B2

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