Réaction #9976

Équation de réaction

Quinoline

5-carboxy-2-(4-fluorophenyl)-3-(pyridin-4-yl)thiophene

→

title compound

Rendement 109.6%

2-(4-Fluorophenyl)-3-(pyridin-4-yl)thiophene

Rendement 109.6%

Conditions de réaction

Traitement

1. 1
   TempératureAt the end of this time, the reaction mixture was cooled to room temperature
2. 2
   Filtrationwas filtered off
3. 3
   AutreThe filtrate was partitioned between ethyl acetate
4. 4
   LavageThe organic layer was washed with water
5. 5
   Séchagedried over anhydrous magnesium sulfate
6. 6
   Autrethe solvent was removed by distillation under reduced pressure
7. 7
   AutreThe residue was purified by column chromatography through silica gel (eluent, hexane:ethyl acetate=1:1)

Mode opératoire

Quinoline (42 ml) and copper powder (2.95 g, 46.4 mmol) were added to 5-carboxy-2-(4-fluorophenyl)-3-(pyridin-4-yl)thiophene (12.64 g (42.2 mmol), prepared as described in 2))), and the resulting mixture was stirred at 240° C. for 2.5 hours. At the end of this time, the reaction mixture was cooled to room temperature and was filtered off. The filtrate was partitioned between ethyl acetate and a saturated aqueous solution of ammonium chloride. The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluent, hexane:ethyl acetate=1:1), to give the title compound (11.81 g) as a brown powder (yield quantitative).

Source