Réaction #1596953

Équation de réaction

bromodibenzofuran

Compound 16-1

bromodibenzofuran

pyrazole

salicylaldoxime

cesium carbonate

→

Compound 17-1

Rendement 78.0%

Pyrazolyldibenzofuran

Rendement 78.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Autreis reacted
2. 2
   Températureunder reflux
3. 3
   Températurewith heating for 6 hours
4. 4
   workup.DISTILLATIONDMF is distilled off from the resulting mixture
5. 5
   Températureby heating under reduced pressure
6. 6
   workup.ADDITIONEthyl acetate is added to the residue
7. 7
   Filtrationthe mixture is filtered with Celite
8. 8
   workup.ADDITIONa 1M sodium hydroxide aqueous solution is added to the obtained liquid
9. 9
   ExtractionOrganic layers extracted from the obtained mixture with ethyl acetate
10. 10
    Séchageare dried with sodium sulfate
11. 11
    ConcentrationThe organic layers are concentrated

Mode opératoire

Under nitrogen current, a mixture containing 12.35 g (50 mmol) of bromodibenzofuran (Compound 16-1), 5.11 g (75 mmol) of pyrazole, 358 mg (2.5 mmol) of cuprous oxide (I), 1.37 g (10 mmol) of salicylaldoxime, 32.6 g (100 mmol) of cesium carbonate, and 100 ml of DMF is reacted under reflux with heating for 6 hours. DMF is distilled off from the resulting mixture by heating under reduced pressure. Ethyl acetate is added to the residue and the mixture is filtered with Celite, and a 1M sodium hydroxide aqueous solution is added to the obtained liquid. Organic layers extracted from the obtained mixture with ethyl acetate are dried with sodium sulfate. The organic layers are concentrated and refined by silica gel column chromatography to obtain 9.12 g (39 mmol) of Compound 17-1.

Source