6-Chloro-N-methoxy-N-methylnicotinamide → HCID 11171599, compound

Temperature

25 °C

To a 0° C. solution of 6-chloro-N-methoxy-N-methylnicotinamide (2 g, 10 mmol) in THF (30 mL) was added the iso-butymagnesium bromide (15 mL of a 1.33M solution in THF, 20 mmol). The reaction mixture was stirred at 25° C. for 2 h. The reaction was quenched by addition of aqueous NH4Cl (30 mL) and extracted with ethyl acetate (30 mL*2). The organic layer was washed with brine (50 mL) and water (50 mL), then dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography to give 1-(6-chloropyridin-3-yl)-3-methylbutan-1-one (1.8 g) as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 8.85 (d, J=2.0 Hz, 1H), 8.12 (dd, J=2.4, 8.4 Hz, 1H), 7.37 (d, J=8.0 Hz, 1H), 2.75 (d, J=6.8 Hz, 2H), 2.26-2.19 (m, 1H), 0.94 (d, J=6.8 Hz, 6H).

1. customThe reaction was quenched by addition of aqueous NH4Cl (30 mL)
2. extractionextracted with ethyl acetate (30 mL*2)
3. washThe organic layer was washed with brine (50 mL) and water (50 mL)
4. dry with materialdried over anhydrous Na2SO4
5. concentrationconcentrated under reduced pressure
6. customThe crude residue was purified by silica gel chromatography

ORD record

ord-b1f9fb6f797948f7bc9cce9ff3739da7

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073871B2