Ammonium Chloride → HCID 59667325, compound

Participants

Reaction Steps

To a stirred solution of 4-chloro-3-(3-nitro-phenoxymethyl)-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester (398 mg, 1.01 mmol) (from Example 2 supra) in 1,4-dioxane (20 mL), THF (10 mL) and DMF (10 mL) was added NH4Cl (810 mg, 15.14 mmol) in water (6 mL). Zinc powder (783 mg, 12 mmol) was then added in several portions and the reaction was stirred at room temperature for a total of 4 hours. The resulting mixture was diluted with ethyl acetate (800 mL), washed with water (100 mL) and then brine (100 mL), dried (Na2SO4) and concentrated. The residue was purified by column chromatography (hexanes/EtOAc, 60/40 to 30/70) to give 3-(3-amino-phenoxymethyl)-thieno[3,2-c]pyridine-7-carboxylic acid ethyl ester as a white solid. (Yield 339.1 mg, 100%).

Provenance & Evidence