Potassium Carbonate → 7-Bromo-1,3-dimethylimidazo[1,5-a]pyridine

HRID 879584Notes

Reaction equation

HRID 879584 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([NH:10][C:11](=O)[CH3:12])[CH3:9])[CH:3]=1.P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:11]([CH3:12])=[N:10][C:8]([CH3:9])=[C:4]2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 24813Phosphorus oxychlorideHCID 86700400N-(1-(4-bromopyridin-2-yl)ethyl)acetamide

Product 1

HCID 838395907-Bromo-1,3-dimethylimidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-(1-(4-bromopyridin-2-yl)ethyl)acetamide (2.28 g, 9.38 mmol) was suspended in anhydrous benzene (20 mL), then phosphorus oxychloride (2.2 mL, 23.6 mmol) was added and the reaction heated to reflux for 3 hours. The crude reaction was then added portion-wise to 1M potassium carbonate solution (60 mL) and stirred until gas evolution ceased. The pH was then adjusted to pH 10 with potassium carbonate. The aqueous layer was extracted with DCM (50 mL×2), the organic were combined, dried over Na2SO4, and concentrated to afford the product, which was used without further purification. LCMS-ESI+: calc'd for C9H10BrN2: 225.1 (M+H+); Found: 225.05 (M+H+).

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 3 hours
  3. customThe crude reaction
  4. extractionThe aqueous layer was extracted with DCM (50 mL×2)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford the product, which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-881d64604e604f5d9789d689afff687c
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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