3-Methylpyridine → HCID 59365480, compound

Temperature

-78 °C

To lithium diisopropyl amide (20 mL, 1.5 M in cyclohexane, 30 mmol) in THF (50.0 mL) at −78° C. was added a solution of 3-picoline (2.79 g, 30 mmol) in THF (25.0 mL) drop wise and stirred at −78° C. for 0.5 hours. The dry ice bath was removed and the reaction mixture was stirred at room temperature 1 hour. The mixture was then cooled to 0° C. and a solution of methyl 2,3-dichlorobenzoate (6.15 g, 30 mmol) in THF (25.0 mL) was added drop wise. The reaction mixture was warmed to room temperature and stirred overnight. The reaction was quenched with ammonium chloride and extracted with ethyl acetate (2×). Combined ethyl acetate phase was washed with brine, dried over magnesium sulfate and concentrated. Purification by chromatography on silica gel (70% ethyl acetate/hexane) gave 1-(2,3-dichlorophenyl)-2-(pyridin-3-yl)ethanone (1.07 g, 13%) as brown oil.

1. customThe dry ice bath was removed
2. stirringthe reaction mixture was stirred at room temperature 1 hour
3. temperatureThe mixture was then cooled to 0° C.
4. temperatureThe reaction mixture was warmed to room temperature
5. stirringstirred overnight
6. customThe reaction was quenched with ammonium chloride
7. extractionextracted with ethyl acetate (2×)
8. washCombined ethyl acetate phase was washed with brine
9. dry with materialdried over magnesium sulfate
10. concentrationconcentrated
11. customPurification by chromatography on silica gel (70% ethyl acetate/hexane)

ORD record

ord-77713a5f473b42b3aa64fbab993aa314

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08183414B2