5-bromo-2-methyl-3H-imidazo[4,5-b]pyridine → HCID 178432171, compound

HRID 1699809Notes

Reaction equation

HRID 1699809 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]=[C:9]([CH3:11])[NH:10][C:5]2=[CH:4][CH:3]=1.[Cu][C:13]#[N:14]>CN(C)C=O>[CH3:11][C:9]1[N:8]=[C:6]2[NH:7][C:2]([C:13]#[N:14])=[CH:3][CH:4]=[C:5]2[N:10]=1

Participants

4

Reactant 2

HCID 223879615-bromo-2-methyl-3H-imidazo[4,5-b]pyridineHCID 178418546HCID 178418546, compound

Product 1

HCID 178432171HCID 178432171, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 5-bromo-2-methyl-1H-imidazo[4,5-b]pyridine (1.92 g) in N,N-dimethylformamide (48 ml) was added Copper (I) cyanide (2.04 g), and the mixture was stirred for 9 hr at 150° C. After evaporation of the solvent under reduced pressure, water (45 ml) and ethylenediamine (2.7 g) were added to the residue, and the mixture was heated at 70° C. for 15 min. The solution was concentrated under reduced pressure and the residue was purified by a short silica gel column to give the objective compound (927 mg) as a brown powder. Purification by silica gel column chromatography (dichloromethane/methanol=10/1) gave a purer compound.

Workup

  1. customAfter evaporation of the solvent under reduced pressure, water (45 ml) and ethylenediamine (2.7 g)
  2. additionwere added to the residue
  3. temperaturethe mixture was heated at 70° C. for 15 min
  4. concentrationThe solution was concentrated under reduced pressure
  5. customthe residue was purified by a short silica gel column

Sources & evidence

ORD record
ord-bf714c75f6774bf59648cff94a937046
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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