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

HRID 653641Notes

Reaction equation

HRID 653641 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]pyridine

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 the title compound.

Workup

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

Sources & evidence

ORD record
ord-e4c98d7ae65d4591b849fe96912872a0
Source dataset
uspto-grants-1992_07
Patent number
US05128327

Reaction notes

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