Ammonium Chloride → N-Methoxy-N-methylthieno[3,2-c]pyridine-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

A suspension of O,N-dimethylhydroxylamine hydrochloride (2.32 g, 23.8 mmol) in THF (20 mL) was purged with N2 and cooled to −78° C. before adding n-butyllithium (1.6 M in hexanes, 30.0 mL, 48.1 mmol). Removed bath and stirred 15 minutes before replacing the bath and adding a solution of thieno[3,2-c]pyridine-2-carboxylic acid methyl ester (0.92 g, 4.76 mmol) in THF (10 mL). After 45 minutes, saturated NH4Cl was added. The mixture was diluted with EtOAc; washed with water, 1 M HCl, water, 5% NaHCO3, water, and brine; dried over Na2SO4, and evaporated to give 0.54 g (51%) of an oil which solidified upon standing. The product thus obtained was used in the next step without further purification. MS m/z 223 (M+H)+.

Provenance & Evidence