Potassium Carbonate → 2-Amino-5-[4-[3-(aminosulfonyl)phenyl]-6-quinolinyl]-3-pyridinesulfonamide

Participants

Reaction Conditions

Reaction Steps

This compound was prepared in one pot (three steps) with no workups between steps. A mixture of 6-bromo-4-chloroquinoline, (484 mg, 2 mmol), bis(pinacolato)diboron, (506 mg, 2 mmol), dichloro-[1,1′bis(diphenylphosphino) ferrocene]palladium (II) dichloromethane adduct (81.5 mg, 0.1 mmol), and potassium acetate (588 mg, 6 mmol) in dioxane (6 mL) was heated at 100° C. for 4 h. To this reaction was added 2-amino-5-bromo-3-pyridinesulfonamide, (560 mg 2 mmol) an equal amount of the palladium catalyst used above (0.1 mmol) and 2 M potassium carbonate (3 mL). The reaction was heated at 95 deg centigrade for one hour. To this reaction was added 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide, (566 mg 2 mmol), dichloro-[1,1′bis(diphenylphosphino) ferrocene]palladium (II) dichloromethane adduct (81.5 mg, 0.1 mmol) and 2 M potassium carbonate (3 mL). The reaction was heated at 95° C. for three hours. The solvent was evaporated and the crude material purified by silica gel chromatography, eluting with ethyl acetate. The product was purified further by crystallizing from hot ethyl acetate. Obtained 181 mg (18.7%) for three steps. MS (ES)+ m/e 484 [M+H]+.

Provenance & Evidence