Dimethylformamide → 2-Methylpyridine-3-carbaldehyde

To a solution of 3-bromo-2-methylpyridine (148; 10 g, 58.1 mmol) in THF (150 mL) was added n-BuLi (2.5 M, 25.6 mL) at −78° C. The reaction mixture was stirred at this temperature for 1 h. DMF (1.30 mL) was then added and the resulting reaction mixture was stirred for 1 h at −78° C. The reaction was quenched by the addition of aq. NH4Cl. Upon warming to room temperature, the mixture was extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography to afford 2-methylnicotinaldehyde 149 (2.18 g, 31%).

1. customthe resulting reaction mixture
2. stirringwas stirred for 1 h at −78° C
3. customThe reaction was quenched by the addition of aq. NH4Cl
4. extractionthe mixture was extracted with EtOAc
5. dry with materialThe combined organic layers were dried (Na2SO4)
6. concentrationconcentrated under reduced pressure
7. customThe resulting residue was purified by chromatography

ORD record

ord-36036a4f8b7f4262b795ea7c2e0e8e9b

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846947B2