Ethyl N,N-dimethyloxamate → HCID 57537465, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-fluoro-pyridine (1 g, 5.68 mmol) in THF (1 mL) was added dropwise to a freshly prepared solution of lithium N,N-diisopropylamide (6.81 mmol) in THF at −78° C. The mixture was stirred 2 h at −78° C. The orange suspension was quickly added via cannula to a cold (−78° C.) solution of N,N-dimethyl-oxalamic acid ethyl ester (925.6 uL 6.81 mmol). After 1.5 h at −78° C., the reaction was quenched by addition of saturated NH4Cl solution and was allowed to warm to room temperature. The mixture was extracted with diethyl ether and the product was purified by silica gel chromatography using hexanes and ethyl acetate (0-100% gradient) to afford 2-(5-bromo-2-fluoro-pyridin-3-yl)-N,N-dimethyl-2-oxo-acetamide (1.01 g, 65.1%). 1H NMR (500 MHz, DMSO-d6) δ 3.0 (d, 6H), 8.6 (dd, 1H), 8.78 (dd, 1H) MS: m/z 275 (M+H+).

Provenance & Evidence