Sodium Hydroxide → 8-(Benzyloxy)-3-bromoimidazo[1,2-a]pyridine

HRID 572978Notes

Reaction equation

HRID 572978 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[N:11]([CH:15]=[CH:16][N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:18]Br.O.[OH-].[Na+]>CCO>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:15]([Br:18])=[CH:16][N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 134329748-(Benzyloxy)imidazo[1,2-a]pyridineHCID 86741833Bromine hydrate

Product 1

HCID 136802018-(Benzyloxy)-3-bromoimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of crude 8-(benzyloxy)imidazo[1,2-a]pyridine (8.73 g, 38.9 mmol) in 100 mL of EtOH was added, dropwise, 4.8 mL (46.7 mmol) of a solution of 1:1 Br2/H2O at ambient temperature under an atmosphere of N2. The resulting dark orange suspension was stirred at ambient temperature for 30 min, added 60 mL 1N NaOH, and the reaction mixture extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated. The crude product was purified by silica gel flash chromatography (eluted with 30% EtOAc/hexanes) to provide 7.04 g of product.

Workup

  1. customat ambient temperature
  2. extractionthe reaction mixture extracted with DCM
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel flash chromatography (eluted with 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-3411236137694dd896f3bc0c0b1d479f
Source dataset
uspto-grants-2015_05
Patent number
US09029533B2

Reaction notes

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