Methyl iodide → HCID 178503348, compound

HRID 82574

Reaction equation

HRID 82574 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[SH:10].CI.[C:13]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH3:13][S:10][C:2]1[NH:3][C:4]2=[N:5][CH:6]=[CH:7][CH:8]=[C:9]2[N:1]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178527819HCID 178527819, compound

Product 1

HCID 178503348HCID 178503348, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1H-imidazo[4,5-b]pyridine-2-thiol (2 g) in acetone (30 mL) were added MeI (0.910 ml) and K2CO3 (5.48 g) at room temperature. After stirring for 10 h, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography (NH-silica gel, eluted with 10%-100% EtOAc in hexane) to give 2-(methylsulfanyl)-3H-imidazo[4,5-b]pyridine (1.0 g) as a white solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was purified by column chromatography (NH-silica gel, eluted with 10%-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-552e96a795fb4545bccf28eb5db15d6d
Source dataset
uspto-grants-2014_09
Patent number
US08846713B2

Linked notes

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