Sodium Methoxide → 5-[3-(Methylsulfonylamino)propylthio]imidazo[1,2-a]pyridine

HRID 5472Notes

Reaction equation

HRID 5472 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]([NH:18][CH2:19][CH2:20][CH2:21]OS(C)(=O)=O)(=[O:17])=[O:16]>C(O)C>[CH3:14][S:15]([NH:18][CH2:19][CH2:20][CH2:21][S:1][C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1)(=[O:17])=[O:16]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 233629523-Methylsulfonylamino-1-methylsulfonyloxypropaneHCID 178418687HCID 178418687, compound

Product 1

HCID 233628535-[3-(Methylsulfonylamino)propylthio]imidazo[1,2-a]pyridineYield 47.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-mercaptoimidazo[1,2-a]pyridine (1.50 g, 10 mmoles) and 4M sodium methylate (2.93 ml, 12 mmoles) in ethanol (50 ml) was added 3-methylsulfonylamino-1-methylsulfonyloxypropane (2.77 g, 12 mmoles) at room temperature and the mixture was heated under reflux for 16 hours. After cooling, the solvent was distilled off. The residue was dissolved in chloroform, washed with an aqueous saturated sodium bicarbonate solution and dried. After the solvent was distilled off, the residue was purified by column chromatography [eluent: ethyl acetate/ethanol (50:1)] to obtain 1.34 g of the desired product (47.5%, pale yellow crystals).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 hours
  3. temperatureAfter cooling
  4. distillationthe solvent was distilled off
  5. dissolutionThe residue was dissolved in chloroform
  6. washwashed with an aqueous saturated sodium bicarbonate solution
  7. customdried
  8. distillationAfter the solvent was distilled off
  9. customthe residue was purified by column chromatography [eluent: ethyl acetate/ethanol (50:1)]

Sources & evidence

ORD record
ord-81bb6d68545c45f9ba9437d6d4437235
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Reaction notes

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