Reaction Steps
To a sealed tube flushed with nitrogen and including DMF (0.5 mL), were added boronic acid 34.1 (90.0 mg, 0.171 mmol), triflate 34.3 (56.6 mg, 0.171 mmol), a 1 M sodium carbonate solution (0.48 mL, 0.480 mmol), lithium chloride (21.7 mg, 0.513 mmol), and Pd(dppf)Cl2 (13.9 mg, 0.0170 mmol). The reaction was heated and stirred at 85° C. for 1.5 hours. The reaction was then cooled and diluted with water. The mixture was extracted with EtOAc (2×50 mL). The organic layers were combined and washed with 1M lithium chloride (1×30 mL) and brine (1×30 mL), and dried over magnesium sulfate. The filtrate was concentrated, and the residue was purified by medium pressure chromatography (silica gel, 0 to 40% EtOAc:hexanes) to give 34.4 (8.90 mg). MS ESI (pos.) m/e: 664.3 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 8.21 (1H, d, J=1.6 Hz), 7.35 (1H, s), 7.09-7.30 (10H, m), 6.86 (2H, d, J=8.6 Hz), 6.06 (1H, d, J=1.6 Hz), 5.98 (1H, s), 4.95 (2H, s), 4.64-4.73 (1H, m), 4.49-4.60 (1H, m), 4.07 (2H, d, J=5.1 Hz), 3.99-4.03 (2H, m, J=2.7 Hz), 3.95 (1H, dd, J=17.6, 8.6 Hz), 3.56 (2H, t, J=5.7 Hz), 3.45 (1H, dd, J=17.4, 6.5 Hz), 3.13 (1H, dd, J=13.3, 3.1 Hz), 2.69 (1H, dd, J=13.5, 9.6 Hz), 2.42-2.50 (2H, m), 1.42 (9H, s).
