Sodium hydride → 4-{2-[2-(3,4-Dimethoxyphenyl)-vinyl]-4,7-dimethoxy-5,6-dimethyl-benzoimidazol-1-ylmethyl}-benzoic acid methyl ester

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Reaction Steps

To a suspension of sodium hydride, 60% dispersion in oil (150 mg; 3.5 mmol) in 20 mL of DMF, {2-[2-(3,4-dimethoxyphenyl)-vinyl]-4,7-dimethoxy-5,6-dimethyl-1H-benzoimidazole (1.2 g; 3.25 mmol) in DMF (20 mL) was added dropwise over 5 minutes. After addition, the reaction mixture was stirred at ambient temperature for 30 minutes, then methyl-4-(bromomethyl)benzoate (745 mg; 3.25 mmol) in DMF (10 mL) was added. The reaction mixture was stirred at ambient temperature for 4 hours. The DMF was concentrated to a residue, and H2O was added. The solid was collected by filtration. Recrystallization from MeOH gave 620 mg (37% yield) of the title compound as a light yellow solid, hemihydrate, m.p. 111-114° C. Anal. Calcd. for C30H32N2O6—0.5 H2O: C, 68.56, H, 6.33; N, 5.33. Found: C, 68.51; H, 6.27; N, 5.28. Mass spectrum: (EI; M+) m/z 516.1H-NMR (DMSO-d6; 400 MHz) δ7.9(d, 2H), 7.72-7.78(d, 1H), 7.31(d, 1H), 7.2-7.26 (m, 4H), 6.95 (d, 1H), 5.9 (s, 2H), 4.12 (s, 3H), 3.81 (s 3H), 3.79 (s, 3H),3.77 (s, 3H), 3.53 (s, 3H), 2.1 ppm (d, 6H).

Provenance & Evidence