Ammonium Hydroxide → 5-Bromo-2-ethyl-7-methyl-1H-imidazo[4,5-b]pyridine

HRID 36099Notes

Reaction equation

HRID 36099 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]=[C:9]([CH2:11][CH3:12])[NH:10][C:5]2=[C:4]([CH3:13])[CH:3]=1.[NH4+].[OH-].[BrH:16].CC(O)=O>>[Br:16][C:2]1[N:7]=[C:6]2[N:8]=[C:9]([CH2:11][CH3:12])[NH:10][C:5]2=[C:4]([CH3:13])[CH:3]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 193857345-chloro-2-ethyl-7-methyl-3H-Imidazo[4,5-b]pyridineHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 193856485-Bromo-2-ethyl-7-methyl-1H-imidazo[4,5-b]pyridine

Conditions

Temperature
100 °C

Procedure

A mixture of 5-chloro-2-ethyl-7-methylimidazo[4,5-b]pyridine (22.2 g, 0.113 mol) in 30% HBr-HOAc was heated to 100° C. for 19 h. The mixture was poured onto ice, neutralized with NH4OH, extracted (5×EtOAc), and the organic layers were concentrated to afford 5-bromo-2-ethyl-7-methylimidazo[4,5-b]pyridine as a solid, after crystallization from EtOAc.

Workup

  1. additionThe mixture was poured onto ice
  2. extractionextracted (5×EtOAc)
  3. concentrationthe organic layers were concentrated

Sources & evidence

ORD record
ord-807e95658b95400389c138c923782db3
Source dataset
uspto-grants-1995_05
Patent number
US05412097

Reaction notes

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