Bromine → N-{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-chloro-2-fluorophenyl}-2,2,2-trifluoroacetamide

Potassium thiocyanate (5.98 g, 61.5 mmol) was dissolved in acetic acid (280 mL), N-{5-[(5-aminopyridin-2-yl)oxy]-4-chloro-2-fluorophenyl}-2,2,2-trifluoroacetamide (5.20 g, 14.9 mmol) was added thereto, and the mixture was stirred at room temperature for 30 min. To the solution was added dropwise a solution (40 mL) of bromine (2.54 g, 15.9 mmol) in acetic acid, and the mixture was stirred at room temperature overnight. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (500 mL), the solution was washed with saturated aqueous sodium hydrogen carbonate solution (200 mL×3) and saturated brine (100 mL), and dried over anhydrous magnesium sulfate. The dried organic layer was concentrated under reduced pressure. The precipitate was collected by filtration to give the title compound (5.78 g, 96%) as a pale-yellow powder.

1. stirringthe mixture was stirred at room temperature overnight
2. filtrationThe reaction mixture was filtered through celite
3. concentrationthe filtrate was concentrated under reduced pressure
4. dissolutionThe residue was dissolved in ethyl acetate (500 mL)
5. washthe solution was washed with saturated aqueous sodium hydrogen carbonate solution (200 mL×3) and saturated brine (100 mL)
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationThe dried organic layer was concentrated under reduced pressure
8. filtrationThe precipitate was collected by filtration

ORD record

ord-1cb384d1a21c4af2ad718fb03e7c1ef1

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344135B2