Sodium Carbonate → 5-(2-Chloro-phenyl)-thiophene-2-carbaldehyde

Participants

Reaction Steps

To a solution of 2-chloro-1-iodobenzene (0.25 mL) and 5-formyl-2-thiophene boronic acid (0.385 g) in DME (8 mL) were added Pd(OAc)2 (0.009 g) and Ph3P (0.021 g) followed by 2M sodium carbonate (1 mL). The mixture was stirred at rt for 1 h. The reaction was diluted with ethylacetate (20 mL) and washed with water and brine, and then dried (sodium sulfate). The crude product was purified by flash-chromatography using EtOAc-hexanes (1:5) to give the desired 5-(2-chlorophenyl)thiophene-2-aldehyde as an oil. The aldehyde (0.15 g), thus obtained, was then condensed with 2,4-thiazolidine-2,4dione in the presence of benzoic acid and piperidine under the conditions described in EXAMPLE 5 to give the title compound 5-(5-(2-chloro-phenyl)thienylidene)thiazolidine-2,4-dione.

Provenance & Evidence