Methanol → 2-[3-(benzyloxy)propyl]-3-methyl-3H-imidazo[4,5-b]pyridine

HRID 333750Notes

Reaction equation

HRID 333750 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[NH:20][C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:23]OS(=O)(=O)OC.CO>CN(C=O)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[N:20]([CH3:23])[C:15]2=[N:16][CH:17]=[CH:18][CH:19]=[C:14]2[N:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 178420422HCID 178420422, compound

Product 1

HCID 895868242-[3-(benzyloxy)propyl]-3-methyl-3H-imidazo[4,5-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under an argon atmosphere, to a solution of 2-[3-(benzyloxy)propyl]-3H-imidazo[4,5-b]pyridine (2 g) in DMF (40 mL) was added 60% sodium hydride (0.299 g), and the mixture was stirred under ice-cooling for 30 min. Then, dimethylsulfuric acid (0.75 mL) was added, and the mixture was stirred at room temperature for 17 hr. To the reaction mixture was added methanol (5 mL), and the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (1.2 g).

Workup

  1. temperaturecooling for 30 min
  2. stirringthe mixture was stirred at room temperature for 17 hr
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-78fd86b8e46e4ae797e11cd5c88aa4e8
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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