Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate → tert-Butyl 4-(((4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinolin-7-yl)oxy)methyl)piperidine-1-carboxylate

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To a mixture of 4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinolin-7-ol HBr salt (1.0 g, 2.4 mmol) and K2SO3 (2.5 g) in DMF (15 mL) at rt was added tert-butyl 4-((methylsulfonyloxy)methyl)piperidine-1-carboxylate (1.0 g, 3.4 mmol, and the reaction mixture was heated at 80-85° C. for 4 h. This mixture was directly purified by flash column chromatography on silica gel eluting with hexane:EtOAc/600:400, and then 300:700 to obtain the desired product (786 mg, 62%) as a glassy solid material. 1H NMR (CDCl3) δ 8.57 (d, 1H, J=5.0 Hz), 8.20 (dd, 1H, J=9.9, 2.8 Hz), 8.13 (dd, 1H, J=8.8, 1.7 Hz), 7.43 (d, 2H, J=2.2 Hz), 7.33 (t, 1H, J=7.7 Hz), 6.54 (d, 1H, J=5.0 Hz), 4.20 (m, 2H), 4.04 (d, 2H, J=6.6 Hz), 4.00 (s, 3H), 2.77 (m, 2H), 2.19-1.89 (m, 3H), 1.47 (s, 9H), 1.34 (m, 2H).

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