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. 2011 Feb 8;54(5):1511–1528. doi: 10.1021/jm1015389

Scheme 3. Synthesis of D-Ring Precursors for 7,9-Disubstituted-8-azatetracyclines.

Scheme 3

Reagents and conditions: (i) for 15a, mCPBA, CH2Cl2; for 15b, H2O2, AcOH, 80 °C; (ii) POBr3, toluene, 100 °C; (iii) BocNH2, Pd2dba3, Xantphos, Cs2CO3, 1,4-dioxane, 80 °C; (iv) HCl, 1,4-dioxane; (v) HF-pyridine, NaNO2, pyridine; (vi) dimethylamine in THF, Pd2dba3, Xantphos, Cs2CO3, 1,4-dioxane, 60 °C (sealed).