Phosphorus oxychloride → 6-Bromo-3-methylimidazo[1,5-a]pyridine

HRID 1399914Notes

Reaction equation

HRID 1399914 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH:9][C:10](=O)[CH3:11])=[N:6][CH:7]=1.O=P(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:10]([CH3:11])=[N:9][CH:8]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 867293001616099-38-7

Product 1

HCID 836814816-Bromo-3-methylimidazo[1,5-a]pyridineYield 70%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N-((5-bromopyridin-2-yl)methyl)acetamide (450 mg, 1.96 mmol) in toluene (15 mL) was added POCl3 (600 mg, 3.92 mmol) and the mixture stirred at refluxing temperature for 6 h. After cooling, the reaction mixture was quenched by adding water (1 mL) and concentrated to remove toluene. The residue was diluted with water (5 mL) and extracted with EtOAc (3×10 mL) with the organic layer concentrated to give a crude product which was used in next step without further purification (290 mg, Yield 70%). LCMS (m/z): 211.0 (M+1)

Workup

  1. temperatureat refluxing temperature for 6 h
  2. temperatureAfter cooling
  3. customthe reaction mixture was quenched
  4. additionby adding water (1 mL)
  5. concentrationconcentrated
  6. customto remove toluene
  7. additionThe residue was diluted with water (5 mL)
  8. extractionextracted with EtOAc (3×10 mL) with the organic layer
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1c3ccc64d64545fe9acff32dea768cdb
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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