Potassium Iodide → HCID 86752041, compound

HRID 861984Notes

Reaction equation

HRID 861984 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([N:9]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]2=[O:19])[CH:4]=1.[P:20]([O:27]CC)([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23].[I-].[K+]>CCC(C)=O>[O:19]=[C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:17](=[O:18])[N:9]1[C:5]1[CH:4]=[C:3]([CH2:2][P:20](=[O:27])([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23])[CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 31215Triethyl phosphiteHCID 197011582-[4-(Bromomethyl)pyridin-2-yl]-1H-isoindole-1,3(2H)-dione

Product 1

HCID 86752041HCID 86752041, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The product from Example 14, triethyl phosphite (7.66 g, 46 mmol) and a catalytic amount of potassium iodide were placed in a flask containing MEK (500 mL) under a N2 atmosphere. The reaction was heated to reflux for 11 h. After cooling to room temperature, the solid was filtered from the reaction mixture, and the filtrate stripped in vacuo. Aqueous K2 CO3 was added to the residue, and the product extracted with EtOAc. The extract was dried (MgSO4), filtered and stripped of all solvent in vacuo to produce the crude product which was purified by flash chromatography (97/3 CHCl3 /EtOH).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 11 h
  3. filtrationthe solid was filtered from the reaction mixture
  4. additionAqueous K2 CO3 was added to the residue
  5. extractionthe product extracted with EtOAc
  6. dry with materialThe extract was dried (MgSO4)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-aa0c6027c20848e992cb3e23d776193c
Source dataset
uspto-grants-1998_02
Patent number
US05716964

Reaction notes

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