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Reagents and conditions: (a) CH2(CO2Me)2, NaH, DMSO, 60 °C, 99%. (b) AcOH, HCl, 110 °C, 99%. (c) EtOH, concentrated H2SO4, reflux, 96%. (d) 3-Nitroaniline, Pd(OAc)2, Xantphos, Cs2CO3, 80 °C, 85%. (e) H2 (balloon), 10% Pd/C, AcOH, room temperature, 72%. (f) R-COOH, HATU, DIEA, DMF, room temperature, 47–99%. (g) 1H-pyrrole-2-carbaldehyde, EtOH, 80 °C, 35–91%.
