Sodium Iodide → Diethyl [[3-chloro-6-(1,3-dihydro-1,3-dioxo-2Hisoindol-2-yl)-2-pyridinyl]methyl]phosphonate

HRID 861990Notes

Reaction equation

HRID 861990 reaction equation
Br[CH2:2][C:3]1[N:8]=[C:7]([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:6]=[CH:5][C:4]=1[Cl:20].[I-].[Na+].[P:23]([O:30]CC)([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26]>CCC(C)=O>[Cl:20][C:4]1[C:3]([CH2:2][P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])=[N:8][C:7]([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:6][CH:5]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 31215Triethyl phosphiteHCID 19701418HCID 19701418, compound

Product 1

HCID 131720462Diethyl [[3-chloro-6-(1,3-dihydro-1,3-dioxo-2Hisoindol-2-yl)-2-pyridinyl]methyl]phosphonate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The product from Example 26 was dissolved in MEK (180 mL) and placed in a 500 mL flask under a N2 atmosphere. Sodium iodide (catalytic) was added to the reaction which was subsequently stirred at room temperature for 20 min. Triethyl phosphite (3.66 g, 22 mmol) was added to the reaction. The reaction was heated to reflux for 6 h, cooled to room temperature, and stirred an additional 16 h. The reaction was filtered and all solvent removed in vacuo to yield the crude title compound. Purification via flash chromatography (96/4 CHCl3 /EtOH) produced the pure title product.

Workup

  1. customplaced in a 500 mL flask under a N2 atmosphere
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 6 h
  4. temperaturecooled to room temperature
  5. stirringstirred an additional 16 h
  6. filtrationThe reaction was filtered
  7. customall solvent removed in vacuo
  8. customto yield the crude title compound
  9. customPurification via flash chromatography (96/4 CHCl3 /EtOH)

Sources & evidence

ORD record
ord-24e97d5714544c86853df936bb679ddf
Source dataset
uspto-grants-1998_02
Patent number
US05716964

Reaction notes

Loading…