Sodium bis(trimethylsilyl)amide → 9-bromo-1-butoxy-3-methylbenzo[c]-1,6-naphthyridin-6(5H)-one

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Reaction Steps

To a solution of 2-(4-amino-2-butoxy-6-methylpyridin-3-yl)-4-bromo-N,N-diisopropylbenzamide (50 mg, 0.10 mmol) in THF (50 mL) was added dropwise a solution of NaHMDS in THF (0.40 mL, 0.20 mmol) at room temperature over 1 h. The resulting mixture was quenched with saturated aqueous NH4Cl solution (3 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine (5 mL), dried over magnesium sulfate, filtered and concentrated to afford a crude solid. The crude material was triturated with diethyl ether (5 mL) and filtered to afford 9-bromo-1-butoxy-3-methylbenzo[c]-1,6-naphthyridin-6(5H)-one. 1H-NMR (300 MHz, DMSO) δ 9.13 (d, J=5.7 Hz, 1H), 8.17 (d, J=8.7 Hz, 1H), 7.47 (dd, J1=8.4 Hz, J2=1.8 Hz, 1H), 4.41 (t, J=6.3 Hz, 2H), 2.27 (s, 3H), 1.82 (m, 2H), 1.60 (m, 2H), 1.00 (t, J=7.5 Hz, 3H). LRMS calc'd for (C17H17BrN2O2) [M+H]+, 361; found 362.

Provenance & Evidence