Potassium Carbonate → Methyl 6-(N-2-picolylaminomethyl)nicotinate

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Commercially available methyl 6-methylnicotinate (2.5116 g) was dissolved in chloroform (50 ml), and N-bromosuccinimide (3.5682 g) and azoisobutylonitrile (290.4 mg) were added to the solution. The mixture was stirred for 22 hours at 70° C. After the reaction, the solvent was removed by distillation. The residue was purified by silica gel column chromatography (100 g, hexane/ethyl acetate=4/1) to obtain a crude product (1.0883 g) as a pale yellow solid. 280.7 mg of the solid (280.7 mg) was dissolved in DMF (5.6 ml), and potassium carbonate (168.5 mg) and 2-picolylamine (0.370 ml) were added. The mixture was stirred for 12 hours at room temperature. After the reaction, the solvent was removed by distillation. The residue was dissolved in chloroform, washed with distilled water, and dried over anhydrous sodium sulfate. The solvent was removed by distillation, and then the residue was purified by silica gel column chromatography (25 g, chloroform/methanol 25/1) to obtain the title compound (298.3 mg) as a pale yellow oil.

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