Réaction #2146692

Équation de réaction

4′-benzoyloxy-2-bromoacetophenone

2-amino-5-methoxypyridine

sodium hydrogencarbonate

→

2-(4′-benzoyloxyphenyl)-6-methoxyimidazo[1,2-a]pyridine

Rendement 70.7%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   TempératureThe resulting solution was refluxed for 2 hours
2. 2
   TempératureAfter the reaction solution was cooled
3. 3
   AutreThe resulting reaction mixture
4. 4
   Températurewas further refluxed for 4 hours
5. 5
   AutreAfter the completion of the reaction
6. 6
   Concentrationthe solvent was concentrated under reduced pressure
7. 7
   workup.DISSOLUTIONThe resulting residue was dissolved in chloroform
8. 8
   Lavagewashed with water
9. 9
   SéchageAfter the chloroform layer was dried over anhydrous sodium sulfate
10. 10
    workup.DISTILLATIONthe solvent was distilled off
11. 11
    AutreThe resulting crude product was purified by silica gel column chromatography (elution solvent: chloroform/ethyl acetate=20/1)

Mode opératoire

13.33 g (corresponding to 43.68 mmol) of 4′-benzoyloxy-2-bromoacetophenone and 5.67 g (corresponding to 45.67 mmol) of 2-amino-5-methoxypyridine were dissolved in 481 mL of ethanol. The resulting solution was refluxed for 2 hours. After the reaction solution was cooled, 6.64 g (corresponding to 79.09 mmol) of sodium hydrogencarbonate was added thereto. The resulting reaction mixture was further refluxed for 4 hours. After the completion of the reaction, the solvent was concentrated under reduced pressure. The resulting residue was dissolved in chloroform and then washed with water. After the chloroform layer was dried over anhydrous sodium sulfate, the solvent was distilled off. The resulting crude product was purified by silica gel column chromatography (elution solvent: chloroform/ethyl acetate=20/1) to obtain 10.20 g (corresponding to 30.87 mmol) of 2-(4′-benzoyloxyphenyl)-6-methoxyimidazo[1,2-a]pyridine (FIG. 3, Step 5).

Source