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Example 9: Synthesis of 3-aminomethyl-2-fluoropyridine (20) 0.3 g (2.46 mmol) of 2-fluoro-3-cyanopyridine (19) was added to a round-bottomed flask and dissolved in 20 mL of anhydrous ethanol. The solution was displaced three times with argon to remove air. Under argon protection, 60 mg of 10% Pd/C catalyst (20 wt% loading) was added. The reaction system was then sealed with a rubber septum and connected to a vacuum pump to evacuate the system. Hydrogen was charged into the system via a balloon and the reaction mixture was stirred at room temperature for 3 h (the reaction progress was monitored by thin layer chromatography (TLC)). Upon completion of the reaction, the system was again evacuated and then air was slowly introduced to terminate the reaction. The reaction mixture was filtered through a diatomaceous earth pad (care was taken to keep the catalyst moist) and the filtrate was concentrated by rotary evaporator to give 0.28 g (90% yield) of 3-aminomethyl-2-fluoropyridine (20) as a colorless oil.

[1] Patent: WO2006/108103, 2006, A1. Location in patent: Page/Page column 31
[2] Patent: US2008/119496, 2008, A1. Location in patent: Page/Page column 10
[3] Patent: WO2008/60301, 2008, A1. Location in patent: Page/Page column 30