반응 #1532271

반응 방정식

1-Methyl-1-propenyl magnesium bromide

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

Ammonium chloride

→

titled compound

수율 32.0%

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

수율 32.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGstirred overnight
2. 2
   추출was then extracted with ethyl acetate
3. 3
   건조The resulting organic layer was dried on anhydrous magnesium sulfate
4. 4
   여과filtered
5. 5
   농축The resulting filtrate was concentrated under reduced pressure
6. 6
   기타The resulting residue was purified with silica gel column chromatography
7. 7
   기타The resulting product was crystallized with ethyl ether

실험 절차

1-Methyl-1-propenyl magnesium bromide (0.5M in tetrahydrofuran solution; 138 ml, 68.9 mmol) was slowly added at −78° C. to a solution of 2-(6-fluoro-3-nitropyridin-2-yl)-1,2,3,4-tetrahydroisoquinoline (5.38 g, 19.7 mmol) prepared in Step 2 in anhydrous tetrahydrofuran (150 ml). The reaction mixture was stirred for 1 hour at the same temperature, slowly warmed to room temperature, and then stirred overnight. 20% (w/v) Ammonium chloride solution was added to the reaction mixture, which was then extracted with ethyl acetate. The resulting organic layer was dried on anhydrous magnesium sulfate and then filtered. The resulting filtrate was concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography. The resulting product was crystallized with ethyl ether to give the titled compound as red oil. (Yield: 32%)

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