To a solution of ethyl 7-(4-(6-bromopyridin-2-ylcarbamoyl)phenoxy)-6-chlorochroman-4-carboxylate (0.050 g, 0.094 mmol), 3,4-dichlorophenylboronic acid (0.023 g, 0.12 mmol), and sodium carbonate (0.030 g, 0.28 mmol) in toluene (1 ml) and water (0.1 ml) degassed with argon was added tetrakis(triphenylphosphine)palladium (0.0054 g, 0.0047 mmol), and the reaction was heated to 100° C. for 16 hours. The reaction was loaded directly onto silica gel and eluted with a linear gradient of 5-70% EtOAc/hexanes to yield the desired compound (0.051 g, 0.085 mmol, 91% yield).
