1,3-Dichloroacetone → 6-Bromo-2-(chloromethyl)imidazo[1,2-a]pyridine

HRID 322294

Reaction equation

HRID 322294 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[Cl:9][CH2:10][C:11]([CH2:13]Cl)=O>COCCOC>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:13]=[C:11]([CH2:10][Cl:9])[N:1]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 706222-Amino-5-bromopyridine

Product 1

HCID 116228946-Bromo-2-(chloromethyl)imidazo[1,2-a]pyridineYield 10.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2-amino-5-bromopyridine (10.0 g). 1,3-dichloroacetone (7.71 g) and 1,2-dimethoxyethane (40 ml) was stirred at room temperature for 4 hours. The precipitated crystals were collected by filtration, to which ethanol (100 ml) was added and heated under reflux. The reaction mixture was concentrated, diluted with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure to give crystals of 6-bromo-2-chloromethylimidazo-[1,2-a]pyridine (1.48 g, 10%). Recrystallization from ethyl acetate-hexane gave colorless needles, mp 129-130° C.

Workup

  1. filtrationThe precipitated crystals were collected by filtration, to which ethanol (100 ml)
  2. additionwas added
  3. temperatureheated
  4. temperatureunder reflux
  5. concentrationThe reaction mixture was concentrated
  6. additiondiluted with saturated aqueous sodium bicarbonate
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with water
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fb4cf1708f384c6ea2674a91b781cbde
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Linked notes

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