Methyl iodide → HCID 22621974, compound

To dry THF at −78° C. was added diisopropylamine(5.05 g 48 mmol, 7 mL) and then n-butyl lithium. The reaction mixture was stirred for 0.5 h and then ethyl 4-pyridyl acetic acid (7.85 g, 46 mmol) was added, and after sirring for 0.5 h at that −78° C. the reaction temperature was raised to room temperature. DMF (20 mL was added and the reaction mixture cooled to −78° C. again. Methyl iodide(7.07 g, 50.2 mmol, 3.15 mL) was added and the reaction mixture stirred at that temperature for 1 h and then at room temperature overnight. All the volatiles were then stripped off and the reaction mixture was partitioned between water-CH2Cl2. The aqueous phase was washed twice with CH2Cl2. The combined CH2Cl2 phases were dried and evaporated. The crude product was chromatographed on silica gel eluting with 80% EtOAc hexane to give the title compound (7.88 g, MH+ 179).

1. waitafter sirring for 0.5 h at that −78° C.
2. temperaturethe reaction mixture cooled to −78° C. again
3. stirringthe reaction mixture stirred at that temperature for 1 h
4. customat room temperature
5. customovernight
6. customthe reaction mixture was partitioned between water-CH2Cl2
7. washThe aqueous phase was washed twice with CH2Cl2
8. dry with materialThe combined CH2Cl2 phases were dried
9. customevaporated
10. customThe crude product was chromatographed on silica gel eluting with 80% EtOAc hexane

ORD record

ord-ff2b59bd19fb4999af198943d9d5a40a

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06242458B1