Step 1: Synthesis of (5-fluoropyridin-3-yl)methanol
To a solution of 5-fluoronicotinic acid (1.0 g, 7.09 mmol) in tetrahydrofuran (THF, 10 mL) was added triethylamine (TEA, 0.9 mL, 7.73 mmol), followed by dropwise addition of ethyl chloroformate (0.6 mL, 7.73 mmol) at 0 °C. The reaction mixture was stirred at room temperature for 2 h and then filtered and the residue was washed with a small amount of THF. The filtrate was cooled to 0 °C and sodium borohydride (0.67 g, 17.73 mmol) was added followed by slow dropwise addition of water (5 mL). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the mixture was partitioned between ethyl acetate and water. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated to give the crude product. The crude product was purified by silica gel column chromatography to give (5-fluoropyridin-3-yl)methanol (197 mg, 21.8% yield) as a colorless oil.LCMS retention time 0.375 min; LCMS MH+ 128.
