Dimethylformamide → HCID 18426849, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(2-bromothiophen-5-yl)-5,6-dichlorobenzimidazole (100 mg, 0.287 mmol) in tetrahydrofuran (6 mL) was added sodium hydryde (60% oil dispersion; 14 mg, 0.35 mmol) at 0° C. under nitrogen atmosphere. After cooling to −78° C., n-butyllithium (1.6 mol/L in hexane; 0.36 mL, 0.57 mmol), dimethylformamide (0.085 mL, 1.1 mmol) were added, and the mixture was stirred for 10 min. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine and dried on anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (19:1 to 9:1 chloroform/acetonitrle) to afford 2-(2-formylthiophen-5-yl)-5,6-dichlorobenzimidazole (36 mg, 42%).

Provenance & Evidence