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Reagents and conditions: (i) R4COCH3, NaOEt, 60 °C, 2 h; (ii) N2H4·H2O, AcOH, EtOH, reflux, 2 h; (iii) NaOH, 1,4-dioxane/H2O, RT, 20–23 h; (iv) 65% HNO3, conc. H2SO4, 60 °C, 3–4 h; (v) cat. DMF, (COCl)2, DCM, 0 °C, 1 h, then RT, 2 h; (vi) 7 M NH3 in MeOH, 0 °C to RT, 6 h; (vii) 10% Pd/C, H2 (g), EtOH, 60 °C, 6–18 h; (viii) 4-fluorobenzoic acid, TEA, PyBrop, DCE, MW 120 °C, 20 min; (ix) KOtBu, iPrOH, MW 130 °C, 30 min.
