A mixture of 3-(8-chloro-3-phenylcinnolin-4-yl)phenol (0.05 g, 0.15 mmol), 4-bromomethylphenyl acetic acid (0.10 g, 0.44 mmol), sodium carbonate (0.50 g, 4.7 mmol), and potassium iodine (0.50 g, 3.0 mmol) in DMF (5 mL)/water (1 mL) was heated to 40° C. for 2 hours. The mixture was then poured into water, acidified with acetic acid and extracted with ethyl acetate. The organic residue was purified by semi-preparative HPLC (Column: Phenomenex C18 Luna 21.6 mm×60 mm, 5 μM; Solvent A: Water (0.1% TFA buffer); Solvent B: Acetonitrile (0.1% TFA buffer); Solvent Gradient: Time 0: 0% B; 10 min: 100% B; Hold 100% B 5 min. Flow Rate: 22.5 mL/min). The product was collected based on UV absorption and concentrated to give the title compound as a colored solid. MS (ESI) m/z 481; HRMS (ESI, [M+H]+) 481.1329.
