Pd(PPh3)4 (120 mg, 0.1 mmol) was added to a mixture of 5-bromo-7-chloro-2-methylquinolin-6-ol (1D) (345 mg, 1.04 mmol), 4-chlorophenylboronic acid (326 mg, 2.09 mmol) and K2CO3 (2.3 mL 2 M in water, 4.7 mmol) in 1,2-dimethoxyethane (10 mL). The reaction mixture was flushed with nitrogen, heated at 80° C. for 16 hours, and then the volatile component was removed in vacuo. The residue was dissolved in ethyl acetate (100 mL), washed with a NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide 1E as a white solid (147 mg, 47%). LCMS-ESI+ (m/z): 304.2, 306.2 (M+H)+.
