2-Hydroxy benzimidazole → 1-[4,4-Bis(4-fluorophenyl)butyl]-1,3-dihydro-benzoimidazol-2-one

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Reaction Steps

To a suspension of sodium hydride (0.72 g, 18 mmol) in DMF (15.0 mL) was added a solution of 1,3-dihydro-benzoimidazol-2-one (11) (2.6 g, 20.0 mmol, Aldrich) in DMF (10.0 mL) at room temperature. The resulting mixture was stirred at room temperature for 30 minutes and a solution of compound 2 (2.8 g, 10 mmol) in DMF (10.0 mL) was added. The resulting mixture was stirred at 60° C. for 4 hours. After this period, the mixture was cooled to room temperature and quenched with water (20 mL). The mixture was extracted with ethyl acetate (100 mL×3). The organic layer was dried with anhydrous Na2SO4 and concentrated to give a crude sample. The crude sample was purified by column chromatography using ethyl acetate/hexane gradient as an eluent to give the title compound 12. MS: m/z 379. 1H NMR (CDCl3): δ 9.41 (s, 1H), 7.10 (m, 8H), 6.92 (t, J=8 Hz, 4H), 3.93 (m, 3H), 2.07 (m, 2H), 1.73 (m, 2H).

Provenance & Evidence