5-[(4-fluorophenyl)methyl]-3-{[4-(methyloxy)phenyl]amino}-2-pyridinecarboxylic acid (560 mg, 1.59 mmol) was dissolved in N,N-dimethylformamide (50 mL) and potassium carbonate (483 mg, 3.50 mmol) and iodomethane (0.15 mL, 2.39 mmol) were added. The reaction was stirred at ambient temperature for 3 hours, diluted with ethyl acetate and water, and extracted with ethyl acetate. The organics were dried over sodium sulfate and concentrated under reduced pressure. Purification by silica gel chromatography (20-100% ethyl acetate/hexanes gradient elution) gave methyl 5-[(4-fluorophenyl)methyl]-3-{[4-(methyloxy)phenyl]amino}-2-pyridinecarboxylate (373 mg, 64% yield) as a white solid. 1H NMR (CDCl3) δ 9.22 (s, 1 H), 7.89 (s, 1 H), 7.09-7.02 (m, 4 H), 6.96-6.86 (m, 4 H), 3.97 (s, 2 H), 3.82 (s, 3 H), 3.80 (s, 3 H); MS m/z 367 (M+1).
