Acetic Acid → HCID 130473159, compound

Participants

Reaction Steps

A stirred solution of [(1S)-2-(3,5-dichloro-1-oxidopyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl]5-formylthiophene-2-carboxylate (128 mg, 0.265 mmol) in dichloromethane (5 mL) was added with 2-fluoroaniline (29 mg, 0.265 mmol) followed by glacial acetic acid (0.015 mL, 0.265 mmol). The reaction was stirred at room temperature for 6 h. Sodium triacetoxyborohydride (140 mg, 0.662 mmol) was added and the reaction was stirred at room temperature for 18 h. Water was added to quench the reaction and the organic layer was washed with brine, passed through a hydrophobic frit and the solvent was removed in vacuo. The crude material was purified by silica gel column chromatography, eluting with 0-100% EtOAc in DCM, to afford the title compound (50 mg, 32%) as a yellow oil.

Provenance & Evidence