Acetic Acid → HCID 71117429, compound

Participants

Reaction Steps

Methyl 2-amino-1-(4-fluorophenyl)-1H-imidazole-5-carboxylate (67) (200 mg, 0.85 mmol), 2,3,6-trifluorobenzaldehyde (163 mg, 1.02 mmol), sodium triacetoxyborohydride (450 mg, 2.13 mmol) and catalytic amounts of acetic acid in acetonitrile (5 mL) was heated under microwave radiation for 2 hours. The reaction mixture was quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-100% EtOAc in hexanes) to afford methyl 1-(4-fluorophenyl)-2-((2,3,6-trifluorobenzyl)amino)-1H-imidazole-5-carboxylate (68).

Provenance & Evidence