반응 #636604

반응 방정식

(E)-3-((R)-4-Pyrrolidin-2-yl-phenyl)-acrylic acid methyl ester

4-(2-bromo-ethyl)-3,5-dimethyl-1H-pyrazole

potassium carbonate

→

(E)-3-(4-{(R)-1-[2-(3,5-dimethyl-1H-pyrazol-4-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester

용매

acetonitrile

DCM

반응 조건

후처리

1. 1
   온도Cooled to room temperature
2. 2
   여과filtered through a plug of celite
3. 3
   농축Filtrate was concentrated to 110 mL
4. 4
   농축after concentrating

실험 절차

(E)-3-((R)-4-Pyrrolidin-2-yl-phenyl)-acrylic acid methyl ester (697 mg, 3 mmol) and 4-(2-bromo-ethyl)-3,5-dimethyl-1H-pyrazole (734 mg, 3.62 mmol) were dissolved in acetonitrile, potassium carbonate (833 mg, 6 mmol) was added, and the reaction mixture heated under nitrogen at 85° C. for 14 h. Cooled to room temperature, diluted with DCM (20 mL) and filtered through a plug of celite. Wash plug with DCM (30 mL). Filtrate was concentrated to 110 mL and columned on silica with EtOAc/hexane. Product elutes with neat EtOAc, and after concentrating gave (E)-3-(4-{(R)-1-[2-(3,5-dimethyl-1H-pyrazol-4-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester as a tacky, pale yellow solid (804 mg, 2.275 mmol, 75%).

출처