Phosphorus oxychloride → Methyl 8-chloroimidazo[1,5-a]pyridine-7-carboxylate

HRID 2067008Notes

Reaction equation

HRID 2067008 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([CH2:10][NH:11][CH:12]=O)[C:5]=1[Cl:14].P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][N:7]2[CH:12]=[N:11][CH:10]=[C:6]2[C:5]=1[Cl:14])=[O:15]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 59565196HCID 59565196, compound

Product 1

HCID 59565199Methyl 8-chloroimidazo[1,5-a]pyridine-7-carboxylateYield 93.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-chloro-2-formylaminomethyl-isonicotinic acid methyl ester (1.5 g, 6.6 mmol) and phosphorous oxychloride (1.3 mL, 14.2 mmol) in toluene (80 mL) was stirred at 90° C. for 15 minutes, then cooled to room temperature and concentrated under reduced pressure. The residue was partitioned between ethyl acetate and a saturated solution of sodium bicarbonate. The organic layer was separated and washed with water and brine, dried (Na2SO4), filtered and concentrated to give the title compound as a pale yellow solid (1.3 g, 93%). LCMS (method B): RT=2.38 min, [M+H]+=211.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ac620d710175475b82dc3a1707adc922
Source dataset
uspto-grants-2012_10
Patent number
US08293763B2

Reaction notes

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