1-Bromo-4-fluorobenzene → HCID 89938200, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-(2-methylpiperazin-1-yl)butanenitrile hydrochloride (1 g, 4.91 mmol) in 1,4 dioxane (25 ml) at 25° C. was added 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (0.306 g, 0.491 mmol), NaOtBu (1.415 g, 14.73 mmol), 1-bromo-4-fluorobenzene (0.648 ml, 5.89 mmol) and tris(dibenzyllideneacetone)dipalladium (0) [Pd2(dba)3] (0.225 g, 0.245 mmol). The resulting reaction mixture was purged with nitrogen for 10 min in sealed tube and stirred at 100° C. in seal tube for 15 h. Progress of the reaction was monitored by TLC. After completion of reaction, the reaction mixture was cooled to room temperature, filtered through a celite bed, and washed with ethyl acetate (2×20 ml). The filtrate was concentrated under reduced pressure to get crude compound. The crude compound was purified by column chromatography over silica gel (100-200 mesh) using 25% ethyl acetate in hexane as eluent to obtain title compound (0.65 g, 50.7).

Provenance & Evidence