Potassium Carbonate → N-(2-chloro-5-{3-[3-(dimethylamino)-1-piperidinyl]-6-quinoxalinyl}-3-pyridinyl)benzenesulfonamide

Participants

Reaction Steps

A slurry of 1-(7-bromo-2-quinoxalinyl)-N,N-dimethyl-3-piperidinamine (1.2 mmol), bis(pinacolato)diboron (1.30 mmol), potassium acetate (4.80 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (1:1) (0.09 mmol) in 1,4-dioxane (5 ml) was heated at 100° C. After the reaction stirred for 2.5 hours, N-(5-bromo-2-chloro-3-pyridinyl)benzenesulfonamide (1.20 mmol) and 2M solution potassium carbonate (5 ml) was added and continued to stir for 18 hours. The reaction was cooled to ambient temperature, concentrated, redissolved in methanol and purified on reverse phase HPLC (0.1% trifluoracetic acid/water in acetonitrile). The desired fractions were combined, neutralized with saturated sodium bicarbonate, extracted with ethyl acetate (3×20 ml). Combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to give the title compound (52 mg, 10%) as a yellow solid. MS(ES)+ m/e 524.2 [M+H]+.

Provenance & Evidence