반응 #1532273

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2-(6-Chloro-3-nitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline

1-Methyl-1-propenyl magnesium bromide

ammonium chloride

→

titled compound

수율 45.0%

2-(5-chloro-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-7-yl)-1,2,3,4-tetrahydroisoquinoline

수율 45.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   추출The reaction mixture was extracted with ethyl acetate
2. 2
   농축concentrated under reduced pressure
3. 3
   기타The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/10

실험 절차

2-(6-Chloro-3-nitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline (16 g, 56.6 mmol) prepared in Preparation 7 was dissolved in anhydrous tetrahydrofuran (300 ml) under a nitrogen atmosphere. 1-Methyl-1-propenyl magnesium bromide (0.5M in tetrahydrofuran solution, 283 ml, 141.5 mmol) was slowly added at −78° C. to the solution. The reaction mixture was stirred for 2 hours at −20° C. and then 20% (w/v) ammonium chloride solution was added thereto. The reaction mixture was extracted with ethyl acetate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/10, v/v) to give 7.8 g of the titled compound as yellow oil. (Yield: 45%)

출처