Methyl iodide → HCID 492673, compound

Participants

Reaction Steps

To 1-(2,6-difluorobenzyl)-2-(2,6-difluorophenyl)-4-acetamidobenzimidazole (Example 88) (2.44 g, 5.90 mmol) and methyl iodide (0.60 mL, 9.69 mmol) dissolved in THF (30 mL) was added excess NaH. After stirring overnight, the solution was concentrated to dryness, diluted with CH2Cl2, and washed with water, NaHSO4(10% soln) and NaCl (sat. aq). The combined washings were dried (Na2SO4), filtered, and concentrated. The crude product was purified by flash chromatography eluting with 2% methanol in CH2Cl2, yielding 1-(2,6-Difluorobenzyl)-2-(2,6-difluorophenyl)-4-(N-methylacetamido)-benzimidazole (0.89 g, 2.08 mmol, 63% yield). M.p. 155-156° C. 1H NMR (200 MHz, CD2Cl2): δ 7.55 (m, 1H, H4′), 7.48 (br d, J=7.4 Hz, 1H, H5), 7.31 (dd, J=7.4, 7.7 Hz, 1H, H6), 7.27 (m, 1H, H4″), 7.14 (dd , J=1.1, 7.7 Hz, 1H, H7), 7.09 (m, 2H, H3′,5′), 6.84 (m, 2H, H3″,5″), 5.38 (s, 2H, CH2PhF2), 3.34 (s, 3H, NCH3), 1.83 (s, 3H, NAc).

Provenance & Evidence