Trifluoroacetic acid → HCID 22382033, compound

Temperature

77.5 °C

To a solution of 1,4-dimethyl-6-(trifluoromethyl)-1H-pyridin-2-one (1.44 g, 7.23 mmol), trifluoroacetic acid (9 mL) and trifluoroacetic anhydride (1.53 mL, 10.85 mmol) was added NIS (2.569 g, 10.85 mmol) at room temperature. Then, the mixture was heated to 70-85° C. and was stirred for 2 h. The reaction mixture was cooled to room temperature and saturated sodium carbonate solution was added slowly to neutralize the solution. Then, the aqueous mixture was extracted with ethyl acetate (2×50 mL). The combined extracts were washed successively with saturated sodium thiosulfate solution (100 mL) and brine solution (100 mL) and were dried over anhydrous sodium sulfate. Filtration of the drying agent and concentration of the solvent gave a crude product, which was purified by silica gel chromatography on a Biotage (40 m) column to afford 1.02 g (45% yield) of 1,4-dimethyl-3-iodo-6-(trifluoromethyl)-1H-pyridin-2-one as an amorphous white solid. ES-LRMS: m/z 318.1 (M+H), 381.2 (M+Na+ CH3CN). f) Preparation of N-[(1,1-dimethylethoxyl)carbonyl]-4-[1,4-dimethyl-6-(trifluoromethyl)-2-oxo-3-pyridinyl]-L-phenylalanine methyl ester

1. temperatureThe reaction mixture was cooled to room temperature
2. extractionThen, the aqueous mixture was extracted with ethyl acetate (2×50 mL)
3. washThe combined extracts were washed successively with saturated sodium thiosulfate solution (100 mL) and brine solution (100 mL)
4. dry with materialwere dried over anhydrous sodium sulfate
5. filtrationFiltration of the drying agent and concentration of the solvent
6. customgave a crude product, which
7. customwas purified by silica gel chromatography on a Biotage (40 m) column

ORD record

ord-0d3d1a2676fb45ae9c31576fd99a6182

Source dataset

uspto-grants-2005_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06916933B2