tert-Butyl N-[[4-[5-[2-[bis(tert-butoxycarbonyl)amino]-5-bromo-3-pyridyl]-1,3,4-oxadiazol-2-yl]phenyl]methyl]-N-methyl-carbamate (120 mg, 0.1817 mmol) was dissolved in DMF (1.2 mL) and 2-(4-isopropylsulfonylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (84.57 mg, 0.2726 mmol) and Pd(PPh3)2Cl2 (7.516 mg, 0.01817 mmol) were added. 2M aqueous Na2CO3 (272.6 μL, 0.5451 mmol) was added and the reaction heated at 80° C. for 1 hour in a sealed tube. The reaction mixture was cooled to ambient temperature and diluted with EtOAc/water. The layers were separated and the aqueous layer extracted with EtOAc (×2). The combined organic extracts were washed with water (×3), brine (×2), dried (MgSO4), filtered and concentrated in vacuo. The resultant residue was purified by column chromatography (ISCO Companion™, 4 g column, 0-50% EtOAc/Petroleum ether) to give the impure sub-title compound as a yellow oil (136 mg). This was used directly in the next step with no further purification.
