Benzyl Bromide → 3-Benzyl-5-bromo-2-ethyl-7-methylimidazo[4,5-b]pyridine

HRID 1492622Notes

Reaction equation

HRID 1492622 reaction equation
[Br:1][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.[H-].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C>[CH2:16]([N:8]1[C:6]2=[N:7][C:2]([Br:1])=[CH:3][C:4]([CH3:13])=[C:5]2[N:10]=[C:9]1[CH2:11][CH3:12])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 193856485-Bromo-2-ethyl-7-methyl-1H-imidazo[4,5-b]pyridine

Product 1

HCID 193856613-Benzyl-5-bromo-2-ethyl-7-methylimidazo[4,5-b]pyridineYield 100.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 10 g (39 mmol) of the product of Step C in DMF (70 mL) at rt was added NaH (1.3 g of an 80% oil dispersion, 43 mmol). After 20 minutes benzyl bromide (5.15 mL, 43 mmol) was added and the reaction was stirred for 16 hours. The mixture was poured onto 500 g of ice and the solid residue was filtered, washed with water and air dried to give 13 g of the title compound.

Workup

  1. filtrationthe solid residue was filtered
  2. washwashed with water and air
  3. customdried

Sources & evidence

ORD record
ord-50c613d085e14b20872999e3ef77e0c8
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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