Ethyl bromopyruvate → HCID 59251305, compound

Participants

Reaction Conditions

Reaction Steps

To a 250 mL round bottom flask attached with condenser was added N-(4-Bromo-phenyl)-2-isopropyl-benzamidine (1.94 g, 6.11 mmol), ethyl bromopyruvate (1.54 mL, 12.2 mmol), sodium bicarbonate (1.02 g, 12.2 mmol), and iso-propanol (45 mL). The reaction slurry was allowed to stir at 80° C. for approximately 2 hrs. The reaction solution was decanted into a clean round bottom flask and concentrated in vacuo. The resulting residue was dissolved in acetic acid (25 mL), and the solution was allowed to stir at reflux for approximately 2 hrs. The solution was concentrated in vacuo, and the product residue was taken into EtOAc (200 mL) and washed with aq NaCl (200 mL×2) and aq NaHCO3 (100 mL). The organic phase was partitioned, dried over Na2SO4, filtered, concentrated, and chromatographed through a 40 g SiO2 column using a mobile gradient of 100% Hx to 70% EtOAc to afford 1.90 g (75% yield) of title compound. MS (ES): 414.0 [M+H]+.

Provenance & Evidence