4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (0.500 g, 2.28 mmol), 3,6-dichloropyridazine (0.340 g, 2.28 mmol), sodium carbonate (0.726 g, 6.85 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.068 g, 0.059 mmol) were mixed in 1,2-dimethoxyethane (11 mL) and water (3.8 mL) under nitrogen. The reaction mixture was heated (110° C.) for 12 h, cooled to RT, diluted with brine, and extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered, and concentrated under vacuum to a crude solid which was dissolved in DCM and extracted into 1N HCl (aq). The DCM layer was discarded, and the aqueous layer was basified with 1N NaOH (aq) and re-extracted with EtOAc. The EtOAc layer was dried (Na2SO4), filtered, and concentrated under vacuum to give the title compound (0.395 g). MS (ESI+) for m/z 206 (M+H)+.
