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

HRID 875217
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HRID 875217 반응식
[CH3:1][N:2]1[C:6]([C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][OH:9])=[CH:5][N:4]=[C:3]1[CH3:16].Br[CH2:18][C:19]1[N:24]=[C:23]([N:25]2[C:33](=[O:34])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]2=[O:35])[CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C>[CH3:1][N:2]1[C:6]([C:7](=[N:8][O:9][CH2:18][C:19]2[N:24]=[C:23]([N:25]3[C:26](=[O:35])[C:27]4[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:33]3=[O:34])[CH:22]=[CH:21][CH:20]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][N:4]=[C:3]1[CH3:16]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 112323512-(6-Bromomethyl-pyridin-2-YL)-isoindole-1,3-dioneHCID 866507511-(1,2-dimethyl-1H-imidazol-5-yl)-N-hydroxy-1-phenylmethanimine

생성물 1

HCID 866507522-{6-[({[(1,2-dimethyl-1H-imidazol-5-yl)(phenyl)methylene]amino}-oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione수율 17.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 1-(1,2-dimethyl-1H-imidazol-5-yl)-N-hydroxy-1-phenylmethanimine (2.29 g, 10.6 mmol) and 2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (3.71 g, 11.7 mmol) in acetonitrile (100 mL) were added cesium carbonate (7.27 g, 22.3 mmol) and potassium iodide (176 mg, 1.06 mmol). After stirring at room temperature for 31.5 h, the reaction mixture was filtered, the insolubles washed with dichloromethane, and the filtrate concentrated in vacuo. Purification on silica gel afforded 2-{6-[({[(1,2-dimethyl-1H-imidazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione [848 mg, yield 16%; HPLC/MS: m/z=452 (M+H); log P(HCOOH)=1.84].

후처리

  1. filtrationthe reaction mixture was filtered
  2. washthe insolubles washed with dichloromethane
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification on silica gel

출처 및 근거

ORD 기록
ord-f53c2665eced4bafa276756da1b1a9ae
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08981111B2

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