반응 #170715

반응 방정식

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

8-quinolinol

1-chloro-4-iodobenzene

cesium carbonate

→

titled compound

수율 96.5%

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

수율 96.5%

용매

N-methylpyrrolidone

toluene

반응 조건

후처리

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

실험 절차

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).

출처