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

HRID 1046533Notes

Reaction equation

HRID 1046533 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>CCO.O.[OH-].[Na+]>[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

6

Reactant 2

HCID 24408BromineHCID 134329748-(Benzyloxy)imidazo[1,2-a]pyridine

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 8-benzyloxy-imidazo[1,2-a]pyridine (25.46 g) in EtOH (250 mL) was added Br2 (7.03 mL) in water (7 mL) dropwise at RT. The resulting dark orange suspension was stirred at RT for 1 h. The reaction mixture was diluted with NaOH (90 mL, 1 N) and extracted with DCM. The organic layer was dried over Na2SO4, filtered, and concentrated. The product crashed in the column and tubing during attempted purification. Recovered product provided 8-benzyloxy-3-bromo-imidazo[1,2-a]pyridine (21 g).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurification

Sources & evidence

ORD record
ord-377eb2ca6be046caabb3f0e5248f0989
Source dataset
uspto-grants-2013_10
Patent number
US08569306B2

Reaction notes

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