Sodium hydride → HCID 22482469, compound

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Reaction Steps

To 2-(2,6-difluorophenyl)-4-methylbenzimidazole (Example 13) (0.50 g, 2.05 mmol) and 3,3-dimethylallyl bromide (0.50 mL, 4.34 mmol, 210 M %) dissolved in THF (10 mL) was added NaH (60% dispersion in mineral oil) (0.17 g, 4.25 mmol, 200 M %). After 4 h, the reaction was quenched with MeOH and concentrated. The residue was redissolved in dichloromethane, washed with water and NaCl (sat. aq.), dried (Na2SO4), filtered and concentrated. The product was purified by flash chromatography eluting with 2% MeOH/CH2Cl2 and recrystallized from hexane to yield white powders of 1-(3,3-dimethylallyl)-2-(2,6-difluorophenyl)-4-methylbenzimidazole (0.40 g, 1.28 mmol, 63% yield). M.p. 78-79° C. 1H-NMR (200 MHz, CD2Cl2): 7.52 (m, 1H, H4″), 7.26-7.02 (m, 5H, H5,6,7,3″,5″), 5.18 (t, J=6.8 Hz, 1H, H2′), 4.62 (d, J=6.8 Hz, 2H, H1′), 2.64 (s, 3H, CH3), 1.64 (s, 3H, CH3), 1.57 (s, 3H, CH3).

Provenance & Evidence