تفاعل #83218

ord-1eb6773bd68e43db9cb10fb39ab16f0c

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.STIRRINGAfter stirring of the mixture for 1 hour at ambient temperature
  2. 2
    استخلاصthe separated oil was extracted with dichloromethane
  3. 3
    غسيلThe extract was washed with brine
  4. 4
    أخرىdried
  5. 5
    تركيزconcentrated in vacuo
  6. 6
    workup.DISSOLUTIONThe residue was dissolved in a solution of sodium (138 mg) in ethanol (5 ml)
  7. 7
    درجة الحرارةthe solution was refluxed for 1 hour
  8. 8
    درجة الحرارةThe reaction mixture was cooled
  9. 9
    workup.ADDITIONpoured into water and neutralized with diluted hydrochloric acid
  10. 10
    استخلاصThe separated oil was extracted with dichloromethane
  11. 11
    غسيلthe extract was washed with brine
  12. 12
    أخرىdried
  13. 13
    تركيزconcentrated in vacuo
  14. 14
    أخرىThe residue was crystallized from ethanol

الإجراء التجريبي

To a suspension of sodium hydride (288 mg) in N,N-dimethylformamide (20 ml) was added dropwise a solution of 5-amino-3-(4-fluorophenyl)-4-(pyridin-4-yl)pyrazole (1.524 g) in N,N-dimethylformamide (5 ml) with ice cooling. The mixture was stirred for 30 minutes and to the mixture was added a solution of ethyl chloroacetate (883 mg) in N,N-dimethylformamide (5 ml). After stirring of the mixture for 1 hour at ambient temperature, the reaction mixture was poured into water and the separated oil was extracted with dichloromethane. The extract was washed with brine, dried and concentrated in vacuo. The residue was dissolved in a solution of sodium (138 mg) in ethanol (5 ml) and the solution was refluxed for 1 hour. The reaction mixture was cooled, poured into water and neutralized with diluted hydrochloric acid. The separated oil was extracted with dichloromethane and the extract was washed with brine, dried and concentrated in vacuo. The residue was crystallized from ethanol to yield 2,3-dihydro-6-(4-fluorophenyl)-2-oxo-7-(pyridin-4-yl)-1H-imidazo[1,2-b]pyrazole (178 mg).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05624931uspto-grants-1997_04