tert-Butyl piperazine-1-carboxylate → tert-Butyl 4-(4-fluoro-2-(trifluoromethyl)-phenyl)piperazine-1-carboxylate

Temperature

110 °C

In a 100ml sealtube was added 1-bromo-4-fluoro-2-(trifluoromethyl)benzene (0.91 g, 3.63 mmol), CESIUM CARBONATE (1.775 g, 5.45 mmol), CESIUM CARBONATE (1.775 g, 5.45 mmol), BINAP (0.271 g, 0.44 mmol), TERT-BUTYL 1-PIPERAZINECARBOXYLATE (0.812 g, 4.36 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.200 g, 0.22 mmol) and 18-CROWN-6 (0.115 g, 0.44 mmol). Followed by 15mL toluene. The mixture was degassed by N2 bubbling for 15min. The reaction mixture was heated at 110oC under nitrogen in an oil bath for overnight. The reaction mixture was diluted with ethyl acetate and filtered through celite. The Celite was washed with EtOAC. The EtOAC was concentrated down to give a brown oil. The crude product was purified by silica gel column(40g) and was eluted with 0% EtOAC/Hexane -25% EtOAC/Hexane. Yield: 0.93g Yellow oil. .

ORD record

ord-05c2bb441c604216aeaf67d50ac253bb

Source dataset

750 AstraZeneca ELN dataset

Original link

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