2,2'-Bipyridine → HCID 68109280, compound

Participants

Reaction Conditions

Reaction Steps

3-(3-cyano-4-hydroxy-5-iodobenzoyl)-1,1-dioxo-2,3-dihydro-1,3-benzothiazole (334 mg) was dissolved in N,N-dimethylformamide (3.5 mL), and 2,2′-bipyridine (11 mg), zinc powder (95 mg), nickel bromide (16 mg) and dimethyl disulfide (0.04 mL) were added to the solution, and then the mixture was stirred at 80° C. for 1 hour. 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 (3 mL). Potassium carbonate (298 mg) and dimethylsulfuric acid (0.13 mL) was added to the solution, and then the mixture was stirred at room temperature for 1 hour. Water was added to the reaction solution, and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and 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=2:1) to obtain the title compound (142 mg) as a pale yellow oily substance.

Provenance & Evidence