Sodium Carbonate → GSK-894490A free base

Participants

Reaction Steps

4-Bromo-N-[5-(cis-3,5-dimethyl-1-piperazinyl)-2-(methyloxy)phenyl]benzenesulfonamide (32.96 g, 72.5 mmol) was suspended in 1,2-dimethoxyethane (300 ml) and treated with sodium carbonate (38.4 g, 363 mmol) dissolved in water (150 ml). (5-Methyl-2-furanyl)boronic acid (13.7 g, 109 mmol) and bis(triphenylphosphine)palladium(II) chloride (108 mg, 0.15 mmol) were added and the mixture was heated at reflux for 1.5 hours. The mixture was cooled and diluted with ethyl acetate, charcoal added and the mixture was stirred with charcoal for 45 minutes. The mixture was filtered through celite, the filtrate separated and washed with saturated sodium bicarbonate solution, water (×3), brine, dried over anhydrous sodium sulfate and concentrated to a crude solid, titrated with pentane and filtered. The combined residues were purified by flash chromatography (Biotage Flash 75+L, dichloromethane to 1:10 2M ammonia in methanol: dichloromethane) followed by trituration with pentane to give the title compound (E247). MS (ES+) m/e 456 [M+H]+.

Provenance & Evidence