Potassium Hydroxide → 1-(tert-Butoxycarbonyl)-4-[4-(pyridin-4-yl)benzenesulfonyl]piperazine

Participants

Reaction Steps

To a solution of 1-(4-bromobenzenesulfonyl)-4-(tert-butoxycarbonyl)piperazine (1.00 g) in tetrahydrofuran (50 ml) were added diethyl(pyridin-4-yl)boron (470 mg), tetrabutylammonium bromide (480 mg), potassium hydroxide (625 mg), tetrakistriphenylphosphine palladium (285 mg) and water (800 μl) at room temperature. The resulting mixture was heated under reflux for 1 hour. After allowed to cool down, the reaction mixture was added with ethyl acetate (50 ml) and water (100 ml). The water layer thus separated was extracted with ethyl acetate (50 ml). The organic layers were combined, washed with saturated aqueous NaCl solution (50 ml), dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (methylene chloride:ethyl acetate=1:1), whereby the title compound (540 mg) was obtained as a colorless transparent viscous substance.

Provenance & Evidence