6-Bromoquinoline → HCID 67401202, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of the 6-bromoquinoline (328 mg, 1.6 mmol, TCI America), 1-BOC-piperazine (340 mg, 1.8 mmol, Aldrich), tris(dibenzylideneacetone)dipalladium(0) (75 mg, 0.1 mmol, Strem), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (91 mg, 0.15 mmol, Strem) and sodium-tert-butoxide (252 mg, 2.7 mmol, Aldrich) in toluene (4 mL) was heated at 150° C. in a microwave synthesizer for 13 min. The reaction mixture was cooled to room temperature, diluted with EtOAc (5 mL) and filtered through a Celite® pad. The filtrate was concentrated in vacuo and the residue was dissolved in MeOH (4 mL) and purified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile) to give the title compound as pale-yellow oil. MS (ESI, pos. ion) m/z: 314 (M+1).

Provenance & Evidence