Phosphorus oxychloride → 6-Bromo-2-chloroimidazo[1,2-a]pyridine

HRID 2196437Notes

Reaction equation

HRID 2196437 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:8][C:9](=O)[N:10]=2)[CH:7]=1.O=P(Cl)(Cl)[Cl:14]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([Cl:14])[N:10]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 16751620HCID 16751620, compound

Product 1

HCID 667895266-Bromo-2-chloroimidazo[1,2-a]pyridine

Conditions

Temperature
105 °C

Procedure

A mixture of 1.4 g of 6-bromo-3H-imidazo[1,2-a]pyridin-2-one in 5 ml of POCl3 is heated at 105° C. for 2 hours and then cooled to ambient temperature and concentrated under reduced pressure. The residue is taken up between water and dichloromethane and a 30% aqueous solution of NH4OH is added until a basic pH is obtained. The organic phase is then separated, dried over magnesium sulphate and concentrated under reduced pressure. The residue is then purified by silica gel chromatography, elution being carried out with a dichloromethane/methanol mixture. 760 mg of compound are obtained.

Workup

  1. temperaturecooled to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. additiona 30% aqueous solution of NH4OH is added until a basic pH
  4. customis obtained
  5. customThe organic phase is then separated
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is then purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-16142df1aff54cd38a777d1504a9e006
Source dataset
uspto-grants-2012_12
Patent number
US08338451B2

Reaction notes

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