Sodium Thiosulfate → 2-Benzyl-3-iodo-5-chloro-6-(3,3-ethylenedioxypyrrolidine-1-yl)pyridine

HRID 1359361Notes

Reaction equation

HRID 1359361 reaction equation
[CH2:1]([C:8]1[C:13]([I:14])=[CH:12][CH:11]=[C:10]([N:15]2[CH2:19][CH2:18][C:17]3([O:23][CH2:22][CH2:21][O:20]3)[CH2:16]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:24]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O>[CH2:1]([C:8]1[C:13]([I:14])=[CH:12][C:11]([Cl:24])=[C:10]([N:15]2[CH2:19][CH2:18][C:17]3([O:20][CH2:21][CH2:22][O:23]3)[CH2:16]2)[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 31398ChlorosuccinimideHCID 219422862-Benzyl-3-iodo-6-(3,3-ethylenedioxypyrrolidin-1-yl)pyridine

Product 1

HCID 181824382-Benzyl-3-iodo-5-chloro-6-(3,3-ethylenedioxypyrrolidine-1-yl)pyridineYield 59.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 500 mg of 2-benzyl-3-iodo-6-(3,3-ethylenedioxypyrrolidine-1-yl)pyridine obtained in Example 118c, 174 mg of N-chlorosuccinimide and 5 ml of N,N-dimethylformamide was stirred under heating for 5 hours in an oil bath kept at 60° C. 1 ml of aqueous solution containing 1 mol of sodium thiosulfate was added to the reaction solution, the mixture was partitioned between ethyl acetate and water. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography using 5-10% ethyl acetate/hexane, to give 320 mg of 2-benzyl-3-iodo-5-chloro-6-(3,3-ethylenedioxypyrrolidine-1-yl)pyridine, and then the title compound was obtained in the same procedures as in Example 118d.

Workup

  1. temperatureunder heating for 5 hours in an oil bath
  2. customkept at 60° C
  3. additionwas added to the reaction solution
  4. customthe mixture was partitioned between ethyl acetate and water
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dfb12b625ed44094b6789f86c1074202
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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