Sodium Methoxide → 5-[1-(Methylsulfonyl)-4-piperidylthio]imidazo[1,2-a]pyridine

HRID 1608633Notes

Reaction equation

HRID 1608633 reaction equation
[SH:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.C[O-].[Na+].[CH3:14][S:15]([N:18]1[CH2:23][CH2:22][CH:21](OS(C)(=O)=O)[CH2:20][CH2:19]1)(=[O:17])=[O:16]>C(O)C.CO>[CH3:14][S:15]([N:18]1[CH2:23][CH2:22][CH:21]([S:1][C:2]2[N:7]3[CH:8]=[CH:9][N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH2:20][CH2:19]1)(=[O:17])=[O:16]

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 222730651-(Methylsulfonyl)piperidin-4-yl methanesulfonateHCID 178418687HCID 178418687, compound

Product 1

HCID 200866605-[1-(Methylsulfonyl)-4-piperidylthio]imidazo[1,2-a]pyridineYield 40.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (1.50 g, 10 moles) in ethanol (100 ml) was added a solution of 4.1M sodium methylate (2.44 ml, 10 mmoles) in methanol and the mixture was stirred at room temperature for 10 minutes. To the reaction mixture was added 1-methylsulfonyl-4-methylsulfonyloxypiperidine (2.83 g, 11 mmoles) at room temperature and the mixture was heated under reflux for 14 hours. After the solvent was distilled off, the residue was dissolved in chloroform, which was washed in turn with an aqueous 1N sodium hydroxide solution and water and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography [eluent: ethyl acetate/ethanol (10:1)] to obtain 1.27 g of the desired product (40.8%, light brown solid).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 14 hours
  3. distillationAfter the solvent was distilled off
  4. dissolutionthe residue was dissolved in chloroform
  5. washwhich was washed in turn with an aqueous 1N sodium hydroxide solution and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationAfter the solvent was distilled off
  8. customthe residue was purified by column chromatography [eluent: ethyl acetate/ethanol (10:1)]

Sources & evidence

ORD record
ord-aafba9e9bba34e7697423ff017d1e70c
Source dataset
uspto-grants-1995_03
Patent number
US05395839

Reaction notes

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