Dimethylformamide → 5,6-Dimethoxypyridine-3-carbaldehyde

Temperature

-78 °C

To a solution of 5-Bromo-2,3-dimethoxy-pyridine (43 g) in THF (500 ml) at −78° C. was added n-butyllithium (191 mmol). After stirring for 30 minutes at −78° C. DMF (28.8 g) was added dropwise and the reaction mixture was stirred at −78° C. for 2 hours. The reaction mixture was quenched with NH4Cl (saturated in water, 500 ml). The aqueous layer was extracted with ethyl acetate, the organic phases were washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by chromatography on silica eluting with heptane with increasing amounts of ethyl acetate.

1. stirringthe reaction mixture was stirred at −78° C. for 2 hours
2. customThe reaction mixture was quenched with NH4Cl (saturated in water, 500 ml)
3. extractionThe aqueous layer was extracted with ethyl acetate
4. washthe organic phases were washed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude product was purified by chromatography on silica eluting with heptane with increasing amounts of ethyl acetate

ORD record

ord-d6a0722505a747f7a649d7990e39af4b

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09127007B2