Water → HCID 18426817, compound

Participants

Reaction Steps

To a solution of 5,6-dichloro-2-[5-formyl-1-(4-methylphenyl)sulfonylindol-2-yl]benzimidazole obtained in Example 45 (824 mg, 1.71 mmol) in dimethylformamide (10 mL) were added diisopropylethylamine (0.59 mL, 3.4 mmol) and chloromethyl methyl ether (0.16 mL, 2.1 mmol), and the mixture was stirred at room temperature for 15 h. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure. To the residue were added methanol (80 mL) and 2 mol/L sodium hydroxide (5 mL), and the mixture was heated to reflux for 1 h. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was triturated with ether to afford 5,6-dichloro-2-[5-formylindol-2-yl]-1-(methoxymethyl)benzimidazole (570 mg, 89%).

Provenance & Evidence