Methyl iodide → 6-Ethyl-2-isopropylsulfanyl-nicotinic acid methyl ester

Temperature

-78 °C

After 2-isopropylsulfanyl-6-methyl-nicotinic acid methyl ester (105 mg, 0.46 mmol) was dissolved in THF (3 mL), KHMDS (1 mL, 0.51 mmol) was added slowly thereto at −78° C., and the mixture was stirred for 30 minutes. MeI (72 mg, 0.51 mmol) was added slowly to the reactant at −78° C., and the mixture was stirred at room temperature for 1 hour. The reactant was cooled, diluted with water, and extracted with EtOAc. The organic layer was dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (eluent EtOAc/Hex=1/5) to obtain the title compound (60 mg, 54%).

1. stirringthe mixture was stirred at room temperature for 1 hour
2. temperatureThe reactant was cooled
3. extractionextracted with EtOAc
4. dry with materialThe organic layer was dried with MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by column chromatography (eluent EtOAc/Hex=1/5)

ORD record

ord-dbde14ee73e74ca3b425f4d2a10f5d49

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09447044B2