반응 #86173

반응 방정식

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

tert-butyl N-[(3S)-1-(6-bromo-3-methoxy-2-pyridyl)-3-piperidyl]carbamate

N,N′-Dimethylethylenediamine

potassium carbonate

→

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

수율 58.3%

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 100% EtOAc in DCM

실험 절차

A mixture of 6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridine (0.4734 mmol; 100.0 mg), tert-butyl N-[(3S)-1-(6-bromo-3-methoxy-2-pyridyl)-3-piperidyl]carbamate (0.5681 mmol, 219.5 mg), N,N′-Dimethylethylenediamine (0.4734 mmol; 41.73 mg; 0.0471 mL), copper iodide (0.4734 mmol; 91.08 mg), and potassium carbonate (0.5208 mmol; 72.70 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 100% EtOAc in DCM to afford tert-butyl N-[(3S)-1-[3-methoxy-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate as a tan solid (142.5 mg, 58%).

출처