반응 #86225

반응 방정식

6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridine

tert-butyl N-[(3S)-1-(5-bromo-1-methyl-2-oxo-3-pyridyl)-3-piperidyl]carbamate

N,N′-Dimethylethylenediamine

potassium carbonate

→

tert-butyl N-[(3S)-1-[1-methyl-5-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-oxo-3-pyridyl]-3-piperidyl]carbamate

수율 45.0%

용매

1,4-Dioxane

반응 조건

후처리

1. 1
   기타was purged with Argon
2. 2
   기타sealed
3. 3
   온도The mixture was cooled to room temperature
4. 4
   여과filtered through Celite
5. 5
   농축The filtrate was concentrated
6. 6
   기타the residue was purified on silica
7. 7
   세척eluted with 0 to 6% MeOH in DCM

실험 절차

A mixture of 6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridine (0.49711 mmol; 105 mg), tert-butyl N-[(3S)-1-(5-bromo-1-methyl-2-oxo-3-pyridyl)-3-piperidyl]carbamate (0.59653 mmol; 230.4 mg), N,N′-Dimethylethylenediamine (0.049711 mmol; 4.382 mg; 0.00495 mL), copper iodide (0.49711 mmol; 95.629 mg), and potassium carbonate (0.99422 mmol; 138.79 mg) in 1,4-Dioxane (10 mL) was purged with Argon, then sealed and stirred at 100° C. overnight. The mixture was cooled to room temperature, and then filtered through Celite. The filtrate was concentrated; the residue was purified on silica eluted with 0 to 6% MeOH in DCM to afford tert-butyl N-[(3S)-1-[1-methyl-5-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-oxo-3-pyridyl]-3-piperidyl]carbamate (116. mg, 45%).

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