反応 #2146694

ord-b5a44cd795b54272b4de73317c71bf2c

反応方程式

COCOc1ccc2nc(-c3ccc(OCCCF)cc3)cn2c1
2-[4′-(3″-fluoropropoxy)phenyl]-6-methoxymethoxyimidazo[1,2-a]pyridine
Cl
hydrochloric acid
O
water
Oc1ccc2nc(-c3ccc(OCCCF)cc3)cn2c1
2-[4′-(3″-fluoropropoxy)phenyl]-6-hydroxyimidazo[1,2-a]pyridine
収率 47.1%

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    温度Then, the mixture was refluxed for 23 hours
  2. 2
    温度After the reaction solution was cooled
  3. 3
    抽出extracted twice by a salting-out extraction procedure
  4. 4
    workup.ADDITIONwith addition of sodium chloride
  5. 5
    乾燥The combined chloroform layer was dried over anhydrous magnesium sulfate
  6. 6
    その他The resulting crude product was purified by silica gel column chromatography (elution solvent: chloroform/methanol=10/1)

実験手順

1.18 g (corresponding to 3.57 mmol) of 2-[4′-(3″-fluoropropoxy)phenyl]-6-methoxymethoxyimidazo[1,2-a]pyridine was dissolved in 29 mL of isopropyl alcohol, and 0.59 mL of conc. hydrochloric acid was added thereto. Then, the mixture was refluxed for 23 hours. After the reaction solution was cooled, the solution was poured into water, and extracted twice by a salting-out extraction procedure using chloroform with addition of sodium chloride. The combined chloroform layer was dried over anhydrous magnesium sulfate. The resulting crude product was purified by silica gel column chromatography (elution solvent: chloroform/methanol=10/1), to obtain 481 mg (corresponding to 1.68 mmol) of 2-[4′-(3″-fluoropropoxy)phenyl]-6-hydroxyimidazo[1,2-a]pyridine (hereinafter referred to as Compound 2) (FIG. 3, Step 10).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US08277777B2uspto-grants-2012_10