Potassium Carbonate → Benzyl [4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate

Temperature

100 °C

3.18 g (23.0 mmol) of potassium carbonate were added to a solution of 4.00 g (15.3 mmol) of 4-chloro-2-(5-methoxy-2-oxo-1,2-dihydropyridin-4-yl)benzonitrile and 2.92 ml (18.4 mmol) of benzyl bromoacetate in 53.3 ml of dimethylformamide, and the mixture was then stirred at 100° C. for 45 min. The reaction mixture was cooled to RT and the reaction was ended by adding 530 ml of water and 10.0 g (236 mmol) of lithium chloride. The mixture was extracted three times with 200 ml of ethyl acetate. The combined organic phases were dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. The residue was dissolved in 50 ml of dichloromethane, applied to diatomaceous earth and purified by flash chromatography (120 g cartridge, 80 ml/min, ethyl acetate/cyclohexane gradient). Yield: 3.90 g (61% of theory)

1. temperatureThe reaction mixture was cooled to RT
2. extractionThe mixture was extracted three times with 200 ml of ethyl acetate
3. dry with materialThe combined organic phases were dried over magnesium sulphate
4. filtrationfiltered
5. customthe solvent was removed under reduced pressure
6. dissolutionThe residue was dissolved in 50 ml of dichloromethane
7. custompurified by flash chromatography (120 g cartridge, 80 ml/min, ethyl acetate/cyclohexane gradient)

ORD record

ord-ee94b06db5ee4be4aeede6faed6236f7

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434690B2