Water → 2-ethyl-5,7-dimethyl-3-(4-nitrobenzyl)-3H-imidazo[4,5-b]pyridine

HRID 1890617Notes

Reaction equation

HRID 1890617 reaction equation
[CH2:1]([C:3]1[NH:13][C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2].[OH2:14].[OH-:15].[Li+].O.C[N:19]([CH:21]=O)C>>[CH2:1]([C:3]1[N:13]([CH2:11][C:10]2[CH:9]=[CH:8][C:21]([N+:19]([O-:15])=[O:14])=[CH:6][CH:5]=2)[C:6]2=[N:7][C:8]([CH3:12])=[CH:9][C:10]([CH3:11])=[C:5]2[N:4]=1)[CH3:2]

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 168937Lithium hydroxide, monohydrateHCID 178437439HCID 178437439, compound

Product 1

HCID 104031282-ethyl-5,7-dimethyl-3-(4-nitrobenzyl)-3H-imidazo[4,5-b]pyridineYield 79.1%

Procedure

2-Ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine (U.S. Pat. No. 5,424,432) (3.50 g, 20.0 mmol) was dissolved in DMF (67 mL), and lithium hydroxide monohydrate (1.26 g, 30.0 mmol) was added thereto, followed by stirring at room temperature for 20 minutes. Then, p-nitorobenzylbromide (4.31 g, 20.0 mmol) was slowly added and stirred at room temperature for 30 minutes. Water (130 mL) was added to the reaction mixture and the precipitated crystals were collected by filtration, followed by washing with water. The crystals was dried under reduced pressure to obtain 2-ethyl-5,7-dimethyl-3-(4-nitrobenzyl)-3H-imidazo[4,5-b]pyridine (4.91 g, 15.8 mmol, yield 79.1%).

Workup

  1. additionThen, p-nitorobenzylbromide (4.31 g, 20.0 mmol) was slowly added
  2. stirringstirred at room temperature for 30 minutes
  3. filtrationthe precipitated crystals were collected by filtration
  4. washby washing with water
  5. customThe crystals was dried under reduced pressure

Sources & evidence

ORD record
ord-6876233e8a1848be9de86a44518c6855
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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