Boronic Acid → N-[5-(cis-3,5-Dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-3-fluoro-4-(2-furanyl)benzenesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]-3-fluorobenzenesulfonamide (E105) (150 mg, 0.32 mmol) and 2-furanylboronic acid (71 mg, 0.64 mmol) in DME (3 ml) was added potassium tert-butoxide (320 mg, 2.9 mmol) and tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol) in water (1 ml) and the resulting mixture stirred in a microwave (set at high absorbance) at 100° C. for 30 minutes. The reaction was checked by LC-MS and as starting material was still present (20%) more boronic acid (71 mg, 0.64 mmol) and tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.017 mmol) were added. The mixture was stirred in the microwave (set at high absorbance) at 100° C. for another 30 minutes. The resulting mixture was then purified using an SCX cartridge and mass directed autoprep HPLC to afford the title compound (E307). MS (ES+) m/e 460 [M+H]+.

Provenance & Evidence