2,2'-Bipyridine → HCID 68108455, compound

Participants

Reaction Conditions

Reaction Steps

3-(3-chloro-4-hydroxy-5-iodobenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (1.19 g) was dissolved in N,N-dimethylformamide (9 mL), and 2,2′-bipyridine (32 mg), a zinc powder (262 mg), nickel bromide (45 mg) and dimethyl disulfide (0.09 mL) were added to the solution, and then the mixture was stirred at 80° C. for 1.5 hours. After the reaction solution was filtered, 1N hydrochloric acid was added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was dissolved in N,N-dimethylformamide (6 mL). Potassium carbonate (828 mg) and dimethylsulfuric acid (0.38 mL) was added to the solution, and then the mixture was stirred at room temperature for 14 hours. Water was added to the reaction solution, and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the title compound (203 mg) as a yellow crystal.

Provenance & Evidence