Preparation | 3-amino -6-chloropyridin-2-formic acid (636mg) was suspended in methanol (8mL) and toluene (22mL) was added. The (trimethylsilyl) diazomethane (2.0M hexane solution, 2.4mL) solution was slowly added to the reaction mixture. After stirring at room temperature for 1 hour, another portion (trimethylsilyl) diazomethane (550 μl) was added and the mixture was stirred for another 45 minutes. The reaction mixture was quenched with water and extracted with ethyl acetate 3 times. The combined organic layers were washed with 2N hydrochloric acid, saturated bicarbonate solution and brine, dried with MgSO4 and concentrated in vacuum. The residue was purified by column chromatography (silica gel 60, chloroform/ethyl acetate 50:1) to give 365mg of the title compound as a yellow solid. |