2-Butanone, 3-bromo- → 6-Fluoro-2,3-dimethylimidazo[1,2-a]pyridin-8-amine

HRID 1386084Notes

Reaction equation

HRID 1386084 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([F:9])=[CH:4][N:3]=1.Br[CH:11]([CH3:15])[C:12](=O)[CH3:13]>C(O)C>[NH2:8][C:7]1[C:2]2[N:3]([C:11]([CH3:15])=[C:12]([CH3:13])[N:1]=2)[CH:4]=[C:5]([F:9])[CH:6]=1

Participants

4

Reactant 2

HCID 131422-Butanone, 3-bromo-HCID 222931555-Fluoro-2,3-pyridinediamine

Product 1

HCID 217173636-Fluoro-2,3-dimethylimidazo[1,2-a]pyridin-8-amineYield 37.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,3-diamino-5-fluoropyridine (0.3 g, 2.4 mmol) and 3-bromo-2-butanon (0.36 g, 2.4 mmol) in ethanol (20 ml) was refluxed for 10 h. The solvent was evaporated under reduced pressure. The residue was dissolved in methylene chloride and was treated with a bicarbonate solution. The organic layer was separated, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified with column chromatography on silica gel with methanol:methylene chloride (1:20) as eluent to give 0.16 g (37%) of the title compound.

Workup

  1. temperaturewas refluxed for 10 h
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride
  4. additionwas treated with a bicarbonate solution
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified with column chromatography on silica gel with methanol:methylene chloride (1:20) as eluent

Sources & evidence

ORD record
ord-ad30d2b509a346f2aa5c66a486c90b04
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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