4-(Trifluoromethoxy)benzylamine → 6-((6-((4-(trifluoromethoxy)benzyl)amino)pyridazin-3-yl)oxy)quinolin-2(1H)-one

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To a suspension of 6-((6-chloropyridazin-3-yl)oxy)quinolin-2(1H)-one (0.032 g, 0.117 mmol) in dioxane (2.0 mL) at room temperature was added 4-(trifluoromethoxy)benzylamine (0.091 mL, 0.585 mmol), (R)-(−)-1-[(S)-2-(Dicyclohexylphosphino)ferrocenyl]ethyldi-t-butylphosphine (3.28 mg, 5.85 μmol), palladium (II) acetate (1.313 mg, 5.85 μmol) and sodium-t-butoxide (0.014 mL, 0.164 mmol). The reaction mixture was stirred in a sealed tube at 110° C. overnight, then concentrated under vacuum to a yellow oil. This was purified by prep HPLC to yield 6-((6-((4-(trifluoromethoxy)benzyl)amino)pyridazin-3-yl)oxy)quinolin-2(1H)-one as a white solid (4 mg, 5%). 1H NMR (500 MHz, METHANOL-d4) δ ppm 7.96 (d, J=9.5 Hz, 2H), 7.67-7.34 (m, 8H), 6.68 (d, J=9.6 Hz, 1H), 4.59 (s, 2H). LCMS: R.T.=1.738 min; [M+H]+=429.08.

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