Dichloromethane → HCID 59454390, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-trifluoromethoxy-phenylamine (0.43 g, 1.68 mmol), cesium carbonate (1.65 g, 5.06 mmol), 1,1′-bis(diphenylphosphino)ferrocenepalladium(ii) dichloride, complex with dichloromethane (1:1) (0.08 g, 0.1 mmol) in dry DMF (20 mL) were charged in a round-bottom flask flushed with argon. The flask was evacuated and backfilled with argon. A solution of 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2,3,6-tetrahydro-pyridine (0.45 g, 2.01 mmol) in dry DMF (10 mL) were added to the suspension and the reaction mixture warmed at 80° C. for 3 hours. The reaction mixture was then allowed to cool to room temperature, diluted with water (100 mL) and extracted with DCM (2×50 mL) and the combined organic phases were extracted with 1N HCl solution (50 mL). The aqueous layer was basified by addition of sodium bicarbonate and extracted with EtOAc (2×50 mL). The combined organic phases were dried over anhydrous Na2SO4, the solvent removed under reduced pressure and the crude solid purified by flash chromatography on silica gel (eluant: DCM/MeOH 90/10) to afford the intermediate as a light brown solid (0.3 g, 65% yield)

Provenance & Evidence