Phosphorus oxychloride → 7-Bromoimidazo(1,5-a)pyridine

HRID 2263536Notes

Reaction equation

HRID 2263536 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][NH:9][CH:10]=O)[CH:3]=1.P(Cl)(Cl)(Cl)=O>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:10]=[N:9][CH:8]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 86071649N-((4-bromopyridin-2-yl)methyl)formamide

Product 1

HCID 668886407-Bromoimidazo(1,5-a)pyridine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 10.75 g of N-(4-bromopyridin-2-ylmethyl)formamide in 100 ml of benzene is admixed with 8.43 g of phosphorus oxychloride. The reaction mixture is heated to reflux over 4 hours. The reaction mixture is subsequently cooled to room temperature and concentrated by evaporation, and the residue is admixed with 200 ml of water. The aqueous solution is basified with 1M NaOH and extracted with dichloromethane (3×300 ml). The combined organic phases are washed with 300 ml of water, dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60 F).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux over 4 hours
  3. concentrationconcentrated by evaporation
  4. extractionextracted with dichloromethane (3×300 ml)
  5. washThe combined organic phases are washed with 300 ml of water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-6d245d1369d249e6bb8045c31fd014ed
Source dataset
uspto-grants-2010_12
Patent number
US07851634B2

Reaction notes

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