Bromide ion → N-{5-[3-(4-{[2-(methyloxy)phenyl]sulfonyl}-1-piperazinyl)-6-quinoxalinyl]-3-pyridinyl}cyclopropanesulfonamide

Participants

Reaction Steps

A slurry of 7-bromo-2-(4-{[2-(methyloxy)phenyl]sulfonyl}-1-piperazinyl)quinoxaline (0.96 mmol), bis(pinacolato)diboron (0.54 mmol), potassium acetate (1.16 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (0.05 mmol) in 1,4-dioxane (4 ml) was heated at 100° C. After the reaction stirred for 1 hour, a bromide such as N-(5-bromo-3-pyridinyl)cyclopropanesulfonamide (0.54 mmol) and 2M solution potassium carbonate (4 ml) was added and continued to stir for 1 hour. The reaction was cooled to ambient temperature, separated the organic layer and purified directly on silica by column chromatography (80% ethyl acetate/hexanes). The desired fractions were combined and concentrated to give the title compound (44 mg, 14% yield) as a pale yellow solid. MS(ES)+ m/e 581.3 [M+H]+.

Provenance & Evidence