Bromine → HCID 89815694, compound

Participants

Reaction Conditions

Reaction Steps

Bromine (0.539 mL, 10.52 mmol) was added dropwise to a 0° C. mixture of 2-oxo-1,2-dihydro-1,7-naphthyridine-3-carboxylic acid (1.00 g, 5.26 mmol) in pyridine (25.0 mL). The mixture stirred at 0° C. for 20 minutes and then at room temperature for 18 hours. The reaction was then heated at 50° C. for 18 hours. The reaction mixture was then concentrated to afford a brown solid. This material was partitioned between DCM and saturated aqueous sodium thiosulfate solution. The aqueous phase was separated and extracted with DCM. The combined organic phases were washed with water and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford a brown solid. The resulting material was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-10% MeOH in DCM to afford 3-bromo-1,7-naphthyridin-2(1H)-one (0.562 g, 2.497 mmol, 47.5% yield) as a tan solid. m/z (ESI) 225.0, 227.0 (M+H)+.

Provenance & Evidence