2-Chloro-5-nitropyridine → 2,2,2-trifluoro-N-{2-fluoro-5-[methyl(5-nitropyridin-2-yl)amino]phenyl}acetamide

A solution of 2-chloro-5-nitropyridine (201 mg, 1.27 mmol) and 2,2,2-trifluoro-N-[2-fluoro-5-(methylamino)phenyl]acetamide (300 mg, 1.27 mmol) in N,N-dimethylformamide (1.5 mL) was stirred at 140° C. for 22 hr. The reaction mixture was cooled to room temperature, suspended in ethyl acetate (5 mL), washed with saturated aqueous sodium hydrogen carbonate solution (5 mL) and saturated brine (5 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 crystallized from ethyl acetate/hexane to give the title compound (221 mg, 49%) as yellow crystals.

1. washwashed with saturated aqueous sodium hydrogen carbonate solution (5 mL) and saturated brine (5 ml)
2. dry with materialdried over anhydrous sodium sulfate
3. filtrationThe insoluble material was filtered off
4. concentrationthe filtrate was concentrated under reduced pressure
5. customThe obtained residue was crystallized from ethyl acetate/hexane

ORD record

ord-8caa9093a80449aa8ade28f2f4762bb9

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697874B2