Bromine → HCID 57387080, compound

Participants

Reaction Steps

Potassium thiocyanate (4.30 g, 44.2 mmol) was suspended in acetic acid (50 mL), and the suspension was stirred at room temperature for 30 min. To the obtained solution was added tert-butyl{3-[(5-aminopyridin-2-yl)oxy]phenyl}carbamate (3.33 g, 11.1 mmol), and the mixture was further stirred at room temperature for 10 min. To the obtained solution was added dropwise a solution of bromine (1.85 g, 11.6 mmol) in acetic acid (10 mL) for 10 min or more. After the completion of the dropwise addition, the mixture was stirred at room temperature for 1.5 hr. The yielded yellow solid was filtered off, and washed with acetic acid. The filtrate and the washing solution were combined, and concentrated under reduced pressure. The residue was suspended in ethyl acetate (200 mL), and the suspension was washed with saturated aqueous sodium hydrogen carbonate solution (50 mL) and saturated brine (30 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with ethyl acetate to give the title compound (3.51 g, 88%) as a pale-yellow solid.

Provenance & Evidence