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Reagents and conditions: (a) Pd(dppf)Cl2, toluene/ethanol/NaHCO3 (sat. aq.) (5:1:5) (0.3 M), 85 °C, 12 h; (b) 5-fluoro-2-nitropyridine (4a) or 5-fluoro-4-methyl-2-nitropyridine (4b), KOH, dry DMSO, 0 °C to rt, 5 min to 1 h; (c) Fe, HCl; EtOH/H2O (5:1) (0.1 M), 2 h, reflux. R1 = H, p-F, [3,4]-(OC2H4O); R2 = H, CH3.
