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

Temperature

100 °C

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).

1. customThe resulting reaction mixture
2. customwas purged with nitrogen for 10 min in sealed tube
3. customAfter completion of reaction
4. temperaturethe reaction mixture was cooled to room temperature
5. filtrationfiltered through a celite bed
6. washwashed with ethyl acetate (2×20 ml)
7. concentrationThe filtrate was concentrated under reduced pressure
8. customto get crude compound
9. customThe crude compound was purified by column chromatography over silica gel (100-200 mesh)

ORD record

ord-52fbca6859be4bfca3b4f36964bec35d

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359367B2