Potassium Iodide → HCID 86650762, compound

HRID 875232Notes

Reaction equation

HRID 875232 reaction equation
[CH3:1][C:2]1[C:3]([C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][OH:11])=[N:4][C:5]([CH3:8])=[CH:6][N:7]=1.Br[CH2:19][C:20]1[N:25]=[C:24]([N:26]2[C:34](=[O:35])[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]2=[O:36])[CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>C(#N)C>[CH3:1][C:2]1[C:3]([C:9](=[N:10][O:11][CH2:19][C:20]2[N:25]=[C:24]([N:26]3[C:27](=[O:36])[C:28]4[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:34]3=[O:35])[CH:23]=[CH:22][CH:21]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:4][C:5]([CH3:8])=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 112323512-(6-Bromomethyl-pyridin-2-YL)-isoindole-1,3-dioneHCID 136331256HCID 136331256, compound

Product 1

HCID 86650762HCID 86650762, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1-(3,6-dimethylpyrazin-2-yl)-N-hydroxy-1-phenylmethanimine (3.38 g, 14.9 mmol) and 2-[6-(bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione (5.19 g, 16.4 mmol) in acetonitrile (50 mL) were added cesium carbonate (10.2 g, 31.2 mmol) and potassium iodide (3.70 mg, 22.3 mmol). After stirring at room temperature for 7 h, the reaction mixture was filtered, the insolubles washed with ethyl acetate, and the combined filtrates concentrated in vacuo, diluted in ethyl acetate (150 mL), washed with water (2×150 mL), dried over MgSO4 and concentrated to dryness in vacuo. Purification on silica gel afforded 2-{6-[({[(3,6-dimethylpyrazin-2-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}-1H-isoindole-1,3(2H)-dione [2.79 g, yield 41%; HPLC/MS: m/z=464 (M+H); log P(HCOOH)=3.35].

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe insolubles washed with ethyl acetate
  3. concentrationthe combined filtrates concentrated in vacuo
  4. additiondiluted in ethyl acetate (150 mL)
  5. washwashed with water (2×150 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness in vacuo
  8. customPurification on silica gel

Sources & evidence

ORD record
ord-4b44700eef0b40a7ae99943a0d70fe5e
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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