2-[(4-Fluorophenoxy)methyl]oxirane → 1-[3-(3-Bromo-benzyl)-2-imino-2,3-dihydro-benzoimidazol-1-yl]-3-(4-fluoro-phenoxy)-propan-2-ol

Participants

Reaction Steps

To a solution of 1-(3-bromo-benzyl)-1,3-dihydro-benzoimidazol-2-ylideneamine (0.50 g, 1.66 mmol) in EtOH (30 ml) at rt was added 2-(4-fluoro-phenoxymethyl)-oxirane (278 mg, 1.66 mmol). The reaction was heated to reflux where it was maintained for 24 h. After this time, additional 2-(4-fluoro-phenoxymethyl)-oxirane (278 mg, 1.66 mmol) was introduced and the reaction was heated to reflux where it was left for a further 6 h. The mixture was cooled to rt and concentrated under reduced pressure. Purification by column chromatography on silica eluting with MeOH/dichloromethane (2-5% gradient) provided 1-[3-(3-bromo-benzyl)-2-imino-2,3-dihydro-benzoimidazol-1-yl]-3-(4-fluoro-phenoxy)-propan-2-ol (361 mg, 46%). HPLC-MS 470, 472 [M+1]+.

Provenance & Evidence