N,N'-Dimethylethylenediamine → 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

Participants

Reaction Conditions

Reaction Steps

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%).

Provenance & Evidence