Methyl (S)-3-methyl-1-oxo-1-((S)-2-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidin-1-yl)butan-2-ylcarbamate (396 mg, 0.761 mmol), (1R,3S,4S)-tert-butyl 3-(5-(4-bromophenyl)-1H-imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (382 mg, 0.913 mmol), Pd(PPh3)4 (88 mg, 0.0761 mmol) and K2CO3 (2M in H2O, 0.95 mL, 1.9 mmol) were suspended in DME (4 mL). The reaction mixture was degassed with N2 for 6 min then heated to reflux. After 6.5 h, the reaction mixture was cooled to RT, diluted with MeOH, filtered over a thiol SPE column and concentrated. The crude residue was purified by column chromatography (0% to 30% MeOH/EtOAc) to afford the title compound (461 mg, 83%).
