Hydrochloric Acid → (E)-5-Fluoro-(4-methoxystyryl)-1-(2-pyridyl)-1H-benzimidazole hydrochloride

Participants

Reaction Steps

Free base of the titled compound was prepared from 4-fluoro-2-amino-N-(2-pyridyl)aniline and (E)-4-methoxycinnamoyl chloride according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base was treated with a 10% methanol solution of hydrogen chloride and concentrated to dryness. The residue was recrystallized from ethyl acetate/ethanol to give the titled compound. MW: 381.84; mp: 204.0-206.0° C.; 1H-NMR (CDCl3) δ: 9.01 (1H, d, J=16.1 Hz), 8.86 (1H, dd, J=4.8, 2.0 Hz), 8.18 (1H, ddd, J=7.7, 7.7, 2.0 Hz), 7.83 (1H, dd, J=7.9, 2.3 Hz), 7.76 (1H, d, J=7.9 Hz), 7.69 (1H, dd, J=7.4, 4.8 Hz), 7.59 (2H, d J=8.7 Hz), 7.40 (1H, dd, J=9.0, 4.2 Hz), 7.17 (1H, ddd, J=9.0, 9.0, 2.3 Hz), 6.85 (2H, d, J=8.7 Hz), 6.78 (1H, d, J=16.1 Hz), 3.82 (3H, s).

Provenance & Evidence