Acetic Acid → N2-(4-Bromo-2-methoxy-6-methylphenyl)-N7,N7-bis(2-methoxyethyl)-1-methyl-1H-benzimidazole-2,7-diamine

Participants

Reaction Steps

To a solution of 200 mg (1.66 mmol) of 1,1,3-trimethoxypropane in 25 mL of chloroform was added 5 g (1.66 mmol) of iron (II) chloride on silica (5% by weight) and the slurry was stirred at room temperature for several hours. The slurry was filtered, concentrated in vacuo to about 5 mL and added to a slurry of 200 mg (0.55 mmol) of N2-(4-bromo-2-methoxy-6-methylphenyl)-1-methyl-1H-benzimidazole-2,7-diamine, 1 mL of acetic acid and 2.5 g (5.08 mmol) of MP-CNBH3 in 10 mL of methanol and was stirred overnight. The above aldehyde preparation was repeated each day for 7 days and added to the reaction. The reaction was filtered and concentrated in vacuo to a residue. The residue was purified by flash chromatography eluting with a solution of 40% ethyl acetate/hexanes containing 2% ammonium hydroxide to give 47 mg (18%) of the title compound.

Provenance & Evidence