N-[5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]benzenesulfonamide → N-[5-(3-{4-[2-(methyloxy)phenyl]-1-piperazinyl}-6-quinoxalinyl)-3-pyridinyl]benzenesulfonamide

Participants

Reaction Steps

A slurry of a boronate ester such as N-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinyl]benzenesulfonamide (0.55 mmol), 7-bromo-2-{4-[2-(methyloxy)phenyl]-1-piperazinyl}quinoxaline (0.37 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (0.03 mmol) in 1,4-dioxane (4 ml) and 2M potassium carbonate (aq) (2 ml) was stirred at 100° C. for 18 hours. The reaction was cooled to ambient temperature, the organic layer separated and purified directly on silica by column chromatography (80% ethyl acetate/hexanes). The desired fractions were combined and concentrated to give the title compound (99 mg, 48%) as a yellow solid. MS(ES)+ m/e 553.4 [M+H]+.

Provenance & Evidence