2-Fluoro-5-(trifluoromethyl)aniline → 6-((6,7-Bis(methoxy)-4-quinolinyl)oxy)-n-(2-fluoro-5-(trifluoromethyl)phenyl)-1-naphthalenecarboxamide

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Reaction Steps

Into a 16×100 mm vial was added 3-amino-4-fluorobenzotrifluoride (100 mg, 0.563 mmol), and dichloromethane (1 mL). To this was added 1.5 mL of a stock solution that is both 0.25M 6-(6,7-dimethoxyquinolin-4-yloxy)-1-naphthoyl chloride and 0.5M DMAP in dichloromethane. Reactions was stirred 24 h at RT. The mixture loaded directly onto silica column. Purified using 0 to 100% EtOAc in hexane. Best fractions were pooled, concentrated under reduced pressure to afford the title compound as a yellow oil. MS (ESI, pos. ion) m/z: 537 (M+1). Mass Calc'd for C29H20F4N2O4: 536.47.

Provenance & Evidence