Bromine → HCID 57387080, compound

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.

1. stirringthe mixture was further stirred at room temperature for 10 min
2. additionAfter the completion of the dropwise addition
3. stirringthe mixture was stirred at room temperature for 1.5 hr
4. filtrationThe yielded yellow solid was filtered off
5. washwashed with acetic acid
6. concentrationconcentrated under reduced pressure
7. washthe suspension was washed with saturated aqueous sodium hydrogen carbonate solution (50 mL) and saturated brine (30 mL)
8. dry with materialdried over anhydrous sodium sulfate
9. filtrationThe insoluble material was filtered off
10. concentrationthe filtrate was concentrated under reduced pressure
11. washThe obtained residue was washed with ethyl acetate

ORD record

ord-7ae97243d1c74c0db6f5022176543e74

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344135B2