Dimethylformamide → HCID 57707780, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(bromomethyl)-3-(2-chlorophenyl)-5-(trifluoromethyl)quinoxaline (0.5137 g, 1.279 mmol) and sodium metaperiodate (0.1416 mL, 2.558 mmol) in DMF (8.527 mL, 1.279 mmol) was heated at 150° C. with stirring. After 3 h, the mixture was cooled to room temperature, diluted with EtOAc (100 mL), washed with brine (50 mL×2), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography on a 80 g of Redi-Sep™ column using 0 to 10% gradient of EtOAc in hexane over 10 min, then 10% isocratic of EtOAc for 20 min, then 10 to 40% gradient of EtOAc in hexane over 20 min, then 40% isocratic of EtOAc for 5 min as eluent to give 3-(2-chlorophenyl)-5-(trifluoromethyl)quinoxaline-2-carbaldehyde as a yellow syrup: 1H NMR (400 MHz, DMSO-d6) δ ppm 10.15 (1H, s), 8.66 (1H, dd, J=8.6, 1.2 Hz), 8.52 (1H, d, J=7.0 Hz), 8.18 (1H, t, J=8.0 Hz), 7.53-7.67 (4H, m); LC-MS (ESI) m/z 337.0 [M+H]+.

Provenance & Evidence