Benzene, 1-bromo-3-nitro- → HCID 67390544, compound

Participants

Reaction Conditions

Reaction Steps

A solution of BINAP (0.47 g, 0.75 mmol) and tris(dibenzylideneacetone)dipalladium (0) (0.34 g, 0.37 mmol) in toluene (120 mL) was heated to 90° C. during 15 minutes under nitrogen. The reaction mixture was cooled to 40° C. before adding 1-bromo-3-nitrobenzene (1.89 g, 9.37 mmol), (1S,4S)-2-isopropyl-2,5-diazabicyclo[2.2.1]heptane dihydrochloride (2.0 g, 9.37 mmol) and sodium tert-butoxide (3.14 g, 32.74 mmol). The reaction was heated to 90° C. during 18 hours under nitrogen. After return to room temperature, the reaction was diluted with ethyl acetate and filtered through celite. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with a mixture of DCM/7N NH3 in methanol (96/4) to afford the title compound (1.92 g, 78%).

Provenance & Evidence