반응 #10624

반응 방정식

Intermediate 71

4-(4-bromo-5-isoquinolyl)amino-1-(tert-butoxycarbonyl)piperidine

cesium fluoride

→

title compound

수율 23.9%

4-(4-fluoro-5-isoquinolyl)amino-1-(tert-butoxycarbonyl)piperidine

수율 23.9%

용매

dimethyl sulfoxide

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled to room temperature
2. 2
   여과filtered through Celite
3. 3
   workup.ADDITIONThe residue was added with water (20 ml)
4. 4
   추출extracted with ethyl acetate (20 ml)
5. 5
   세척washed twice with saturated brine (10 ml for each time)
6. 6
   건조The organic layer was dried over anhydrous sodium sulfate
7. 7
   기타the solvent was evaporated under reduced pressure
8. 8
   기타The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

실험 절차

A solution of Intermediate 71 (104 mg) in dimethyl sulfoxide (2 ml) was added with cesium fluoride (284 mg, Wako Pure Chemical Industries) and stirred at 150° C. for 8 hours. The reaction mixture was cooled to room temperature and then filtered through Celite. The residue was added with water (20 ml), extracted with ethyl acetate (20 ml) and washed twice with saturated brine (10 ml for each time). The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (21.1 mg).

출처