Dimethylformamide → HCID 89853000, compound

Participants

Reaction Conditions

Reaction Steps

A solution of n-butyllithium in hexanes (0.3 g, 4.69 mmol) was added dropwise to a solution of 2-(azetidin-1-yl)-6-bromopyridine (0.5 g, 2.34 mmol) in dry tetrahydrofuran (20 mL) at −78° C. After stirring for 30 min at −78° C., N,N-dimethylformamide (0.34 g, 4.69 mmol) was added. The reaction mixture was stirred for 3 h at −78° C., then the reaction mixture was quenched with an aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude material was purified via flash chromatography (60-120 mesh silica; 4-5% ethyl acetate in petroleum ether, twice) to afford 6-(azetidin-1-yl)picolinaldehyde (0.2 g, 43%). MS (ES+) (M+H) 163.1380; LCMS retention time: 5.59 minutes (Method X).

Provenance & Evidence