Ethyl trifluoroacetate → HCID 59240304, compound

Participants

Reaction Conditions

Reaction Steps

To a dry N2 purged 50 mL round bottom flask attached with addition funnel was added 1-(1-(4-bromo-2-chlorophenyl)-2-(2-chlorophenyl)-1H-imidazol-4-yl)ethanone (640 mg, 1.56 mmol) and anhydrous THF (12 mL). The reaction solution was cooled to −78° C. prior to dropwise addition of a 1.0 M LHMDS solution in THF (1.72 mL). The enolate solution was allowed to stir, warming to −200C over 1 h. The reaction solution was cooled to −600C, and ethyl trifluoroacetate (370 μL, 3.12 mmol) was added. The reaction solution was stirred at room temperature for 16 h. The reaction solution was quenched with H2O and diluted with EtOAc (100 mL). The EtOAc phase was partitioned, dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was chromatographed through a 12 g SiO2 column using a 100% hexane to 60% EtOAc gradient to yield 120 mg (86% yield) of title compound. MS (ESI) 507.0, 509.0 [M+H]+.

Provenance & Evidence