Phenylboronic Acid → N-(5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 2-(4-(5-bromo-3-(nicotinamido)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-2-oxoethylcarbamate (0.090 g, 0.16 mmol) and phenylboronic acid (0.039 g, 0.32 mmol) were placed in dioxane (1.5 mL) and degassed for 30 minutes. A 20% Na2CO3 (0.5 mL) solution was then added, followed by the addition of PS-Pd(PPh3)4 (0.081 g, 0.0081 mmol). The reaction was then heated in a microwave at 150° C. for 1 hour. The reaction was next diluted with DCM and filtered to remove the catalyst The reaction was then purified by prep HPLC to give a mixture of tert-butyl 2-(4-(3-(nicotinamido)-5-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)piperazin-1-yl)-2-oxoethylcarbamate (0.013 g, 15% yield) and N-(5-phenyl-4-(piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)nicotinamide (0.020 g, 31% yield).

Provenance & Evidence