Ethyl Acetate → 1-Butoxypyrido[4,3-c]-1,6-naphthyridin-6-yl trifluoromethanesulfonate

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To a mixture of 1-butoxypyrido[4,3-c]-1,6-naphthyridin-6-ol (2 g, 7.43 mmol) and cesium carbonate (4.84 g, 14.85 mmol) in DMA (75 ml), N-phenyltrifluoromethanesulfonamide (5.31 g, 14.85 mmol) was added. The reaction mixture was heated to 80° C. and stirred for 7 min. The reaction was then cooled to room temperature and added to ethyl acetate. The organic mixture was washed with aqueous sodium hydrogen carbonate (saturated), aqueous sodium carbonate (saturated), and brine. The organic extracts were combined, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/hexanes, to afford 1-butoxypyrido[4,3-c]-1,6-naphthyridin-6-yl trifluoromethanesulfonate as a yellow solid. 1H NMR (500 MHz, C2D6SO) δ 10.68 (s, 1H), 9.08 (d, 1H), 8.52 (d, 1H), 8.14 (d, 1H), 7.62 (d, 1H), 4.70 (t, 2H), 1.96 (m, 2H), 1.57 (m, 2H), 1.00 (t, 3H). LRMS (APCI) calc'd for (C16H15F3N3O4S) [M+H]+, 402.1; found 402.0.

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