Reacción #170715

Ecuación de reacción

3-(2,5-dimethylpyrrol-1-yl)-1H-pyrazole

8-quinolinol

1-chloro-4-iodobenzene

cesium carbonate

→

titled compound

Rendimiento 96.5%

1-(4-Chlorophenyl)-3-(2,5-dimethylpyrrol-1-yl)-1H-pyrazole

Rendimiento 96.5%

Disolventes

N-methylpyrrolidone

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat room temperature
2. 2
   TemperaturaThis reaction mixture was cooled to room temperature
3. 3
   Filtraciónthe mixture was filtered through Celite
4. 4
   Lavadofurther subjected to elution with toluene
5. 5
   LavadoThe filtrate was sequentially washed with a 1N aqueous solution of sodium hydroxide, water
6. 6
   Secadoa saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   OtroThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 9/1)

Procedimiento

Under argon atmosphere, to a solution of 3-(2,5-dimethylpyrrol-1-yl)-1H-pyrazole (3.06 g) prepared according to the same procedures as Preparation 4 in N-methylpyrrolidone (31 ml) were sequentially added cesium carbonate (12.37 g), 8-quinolinol (0.55 g), copper (I) oxide (0.27 g) and 1-chloro-4-iodobenzene (6.79 g) at room temperature, the mixture was stirred at 110° C. for 2 hours. This reaction mixture was cooled to room temperature, and then toluene (30 ml) was added thereto, the mixture was filtered through Celite, and further subjected to elution with toluene. The filtrate was sequentially washed with a 1N aqueous solution of sodium hydroxide, water, a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 9/1) to give the titled compound (4.98 g).

Fuente