2,3,6-Trifluoroaniline → ethyl 1-(4-fluorophenyl)-2-(((2,3,6-trifluorophenyl)amino)methyl)-1H-imidazole-5-carboxylate

Participants

Reaction Steps

A solution of ethyl 1-(4-fluorophenyl)-2-formyl-1H-imidazole-5-carboxylate (16) (150 mg, 0.57 mmol), 2,3,6-trifluoroaniline (60.4 μL, 0.57 mmol), decaborane (14 mg, 0.11), acetic acid (2 drops), and methanol (6 mL) was stirred at room temperature overnight. The reaction was concentrated and the residue was purified by flash column chromatography on silica gel (0-30% EtOAc in hexanes) to yield ethyl 1-(4-fluorophenyl)-2-(((2,3,6-trifluorophenyl)amino)methyl)-1H-imidazole-5-carboxylate (23).

Provenance & Evidence