Sodium bis(trimethylsilyl)amide → HCID 178450360, compound

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To a solution of 2-(4-amino-2-butoxypyridin-3-yl)-4-bromo-N,N-diisopropylbenzamide (8.5 g, 19.0 mmol) in THF (135 mL) was added sodium bis(trimethylsilyl)amide (38 mL, 38 mmol, 1.0 M in THF) dropwise at 0° C. under nitrogen. The solution was allowed to stir for 2 hr then quenched with water. The solid precipitate was filtered, collected, and dried under vacuum to afford 9-bromo-1-butoxybenzo[c]-1,6-naphthyridin-6-ol as a white solid. 1H NMR (600 MHz, CD6SO) δ 9.22 (s, 1H), 8.2 (d, 1H), 8.05 (d, 1H), 7.78 (d, 1H), 6.92, (d, 1H), 4.45 (t, 2H), 1.86 (m, 2H), 1.59 (m, 21-1), 1.0 (t, 3H). LRMS (ESI) calc'd for (C16H15BrN2O2) [M+H]+, 347.0; found 347.0.

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