Piperazine → HCID 68594568, compound

Participants

Reaction Steps

Dissolve 2-bromo-3-(4-fluorophenyl)-pyridine (4.4 g, 17.5 mmol) in toluene (185 mL) and add piperazine (4.5 g, 52.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.8 g, 0.873 mmol), sodium-t-butoxide (2.35 g, 24.4 mmol) and racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.63 g, 2.62 mmol). Reflux the mixture for 18 hr.s, then cool to room temperature and filter through Celite®. Dilute the mixture with ethyl acetate and wash with saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 15:85 2 M ammonia in methanol:DCM) to give the title preparation as a yellow solid (3.9 g, 87%). MS (APCI): m/z=258 [M+H]+.

Provenance & Evidence