반응 #591116

반응 방정식

KHSO4 Na2SO4

2-bromobenzonitrile

DIPEA

3-(4-mercapto-2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

→

3-[4-(2-cyano-phenylsulfanyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

수율 90.0%

용매

1,4-dioxane

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도at reflux for 16 hours
3. 3
   온도cooled
4. 4
   추출The mixture was extracted with EtOAc
5. 5
   세척the combined organic extracts were washed with water and brine
6. 6
   건조dried over Na2SO4
7. 7
   여과filtered
8. 8
   기타evaporated under reduced pressure
9. 9
   기타The resulting crude material was purified via flash chromatography (hexane/EtOAc, 7/3)

실험 절차

Pd2(dba)3 (13 mg, 0.01414 mmol), Xantphos (16 mg, 0.02828 mmol), 2-bromobenzonitrile (0.103 mg, 0.5655 mmol) and DIPEA (0.103 mL, 1.131 mmol) were added to a solution of 3-(4-mercapto-2-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.175 g, 0.5655 mmol) in 1,4-dioxane (10 mL). The reaction mixture was heated at reflux for 16 hours, then cooled and a solution of 10% KHSO4/Na2SO4 was added. The mixture was extracted with EtOAc, and the combined organic extracts were washed with water and brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The resulting crude material was purified via flash chromatography (hexane/EtOAc, 7/3) to give 0.209 g (90% yield) of 3-[4-(2-cyano-phenylsulfanyl)-2-methoxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a clear oil.

출처