N,N'-Dimethylethylenediamine → benzyl 1-oxo-2-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution containing 3-iodo-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine (0.196 g, 0.434 mmol), benzyl 1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (0.250 g, 0.867 mmol), N,N′-Dimethylethylenediamine (0.103 mL, 0.954 mmol), Copper(I) iodide (0.0908 g, 0.477 mmol) and Cesium Carbonate (0.311 g, 0.954 mmol) in 1,4-Dioxane (7.08 mL, 90.7 mmol) was stirred at 75° C. for 2 h. The reaction was filtered thru celite and concentrated. The crude product purified by Isco column (EtOAc/Hep eluted at 50% EtOAc) to give benzyl 1-oxo-2-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate (140 mg, 52.7% yield). ESI MS m/z=613.1 (M+1).

Provenance & Evidence