Methyl iodide → HCID 178503348, compound

HRID 1429949Notes

Reaction equation

HRID 1429949 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-0578907c6fa2445e8489e712d58e9225
Source dataset
uspto-grants-2015_01
Patent number
US08940758B2

Reaction notes

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