Acetic acid, (dimethylamino)oxo-, ethyl ester → HCID 57537465, compound

Temperature

-78 °C

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+).

1. waitAfter 1.5 h at −78° C.
2. customthe reaction was quenched by addition of saturated NH4Cl solution
3. temperatureto warm to room temperature
4. extractionThe mixture was extracted with diethyl ether
5. customthe product was purified by silica gel chromatography

ORD record

ord-f8d4e502e54342128f5de76259392917

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158647B2