반응 #10627

반응 방정식

Intermediate 71

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

tetramethyltin

2,6-di-tert-butyl-4-methylphenol

→

title compound

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

용매

toluene

반응 조건

후처리

1. 1
   온도The reaction mixture was cooled to room temperature
2. 2
   여과filtered through Celite
3. 3
   농축concentrated under reduced pressure
4. 4
   workup.ADDITIONThe residue was added with saturated brine (30 ml)
5. 5
   추출extracted three times with ethyl acetate (30 ml for each time)
6. 6
   건조dried over anhydrous sodium sulfate
7. 7
   기타the solvent was evaporated under reduced pressure
8. 8
   기타The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

실험 절차

A solution of Intermediate 71 (313 mg) in toluene (6 ml) was added with tetrakis(triphenylphosphine)palladium(0) (17.9 mg, Aldrich), tetramethyltin (165 μl, Kanto Chemicals) and 2,6-di-tert-butyl-4-methylphenol (several pellets, Tokyo Kasei Kogyo) and stirred in a sealed tube at 150° C. for 48 hours. The reaction mixture was cooled to room temperature, filtered through Celite and concentrated under reduced pressure. The residue was added with saturated brine (30 ml) and extracted three times with ethyl acetate (30 ml for each time). The organic layers were combined and dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain the title compound (61.7 mg).

출처