Sodium hydride → HCID 22482463, compound

Participants

Reaction Steps

To 2-(2,6-difluorophenyl)-4-methoxylbenzimidazole (5005, Example 46) (0.28 g, 1.08 mmol) and 3,3-dimethylallyl bromide (0.20 mL, 0.26 mmol, 160 M %) dissolved in THF (3 mL) was added NaH (60% dispersion in mineral oil) (0.15 g, 3.75 mmol, 350 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 give white powders of 1-(3,3-dimethylallyl)-2-(2,6-difluorophenyl)-4-methoxyl-benzimidazole (0.30 g, 0.91 mmol, 84% yield). M.p. 101-103° C. 1H-NMR (200 MHz, CD2Cl2): 7.52 (m, 1H, H4″), 7.24 (dd, J=7.9, 8.2 Hz, 1H, H6), 7.08 (m, 2H, H3″,5″), 7.02 (dd, J=0.9, 8.2 Hz, 1H, H5), 6.73 (dd, J=0.9, 7.9 Hz, 1H, H7), 5.19 (t, J=7.0 Hz, 1H, H2′), 4.02 (s, 3H, OCH3), 4.62 (d, J=7.0 Hz, 2H, H1′), 1.64 (s, 3H, CH3), 1.58 (s, 3H, CH3).

Provenance & Evidence