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 875217Notes

Reaction equation

HRID 875217 reaction equation
[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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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].

Workup

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

Sources & evidence

ORD record
ord-f53c2665eced4bafa276756da1b1a9ae
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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