반응 #1963425

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KOH

5′-(5-cyano-1-methyl-1H-pyrrol-2-yl)spiro[cyclohexane-1,3′-[3H]indol]-2′-ylidenecyanamide

Pd

N-Acetylcysteine

→

5′-(5-cyano-1-methyl-1H-pyrrol-2-yl)spiro[cyclohexane-1,3′-[3H]indol]

Pd

용매

THF

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후처리

1. 1
   기타a clear orange solution was obtained
2. 2
   여과filtered
3. 3
   workup.ADDITIONTen percent aqueous HCl (3 mL) was added dropwise to the filtrate
4. 4
   기타precipitation of a white solid
5. 5
   여과The solution was filtered
6. 6
   세척the solid washed with methanol
7. 7
   기타the washed solid dried

실험 절차

Crude 5′-(5-cyano-1-methyl-1H-pyrrol-2-yl)spiro[cyclohexane-1,3′-[3H]indol]-2′-ylidenecyanamide (1.0 g) containing residual Pd (5100 ppm) was suspended in THF (5 mL). Upon addition of aqueous 1M KOH (5 mL), a clear orange solution was obtained. N-Acetylcysteine (1.3 g) was added, the mixture was stirred for 1 hour, and filtered. Ten percent aqueous HCl (3 mL) was added dropwise to the filtrate causing precipitation of a white solid. The solution was filtered, the solid washed with methanol, and the washed solid dried to give 5′-(5-cyano-1-methyl-1H-pyrrol-2-yl)spiro[cyclohexane-1,3′-[3H]indol])-2′-ylidenecyanamide (0.6 g; 60% yield; 96 ppm Pd).

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