Acetic Acid → [5-(2-Ethylaminomethyl-4-fluoro-phenyl)-pyridin-3-yl]-acetic acid ethyl ester

Participants

Reaction Steps

To [5-(4-fluoro-2-formyl-phenyl)-pyridin-3-yl]-acetic acid ethyl ester (1.2 g, 4.18 mmol) in MeOH was added sodium cyanoborohydride (0.394 g, 6.26 mmol) and ethylamine (2M in THF; 3.13 mL, 6.26 mmol). Acetic acid (0.36 mL, 6.26 mmol) was added, and the reaction was stirred for 2 hours at room temperature. The mixture was concentrated, and the residue was dissolved in CH2Cl2 and washed with saturated aqueous NaHCO3 and H2O. The organic layer was dried over Na2SO4, filtered, and concentrated, and the residue was purified by silica gel chromatography (0-10% MeOH in CH2Cl2) to give [5-(2-ethylaminomethyl-4-fluoro-phenyl)-pyridin-3-yl]-acetic acid ethyl ester.

Provenance & Evidence