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

HRID 5478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 5478
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 200866605-[1-(Methylsulfonyl)-4-piperidylthio]imidazo[1,2-a]pyridineAusbeute 40,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a suspension of 5-mercaptoimidazo[1,2-a]pyridine (1.50 g, 10 mmoles) 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).

Aufarbeitung

  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)]

Quellen und Nachweise

ORD-Eintrag
ord-b41679ed788043cfae401763920430fc
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244908

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