Cesium carbonate → HCID 67074086, compound

Participants

Reaction Steps

1 g of 3,5-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline (Intermediate 1A; 2.537 mmol, 1 eq.), 194 mg 3-amino-4-fluorophenol (1.522 mmol, 0.6 eq.) and 1.240 g caesium carbonate (3.806 mmol, 1.5 eq.) were suspended in 12 mL DMF and stirred at rt for 72 h. The reaction mixture was partitioned between butan-2-one and half saturated brine. The layers were separated and the aqueous layer was reextracted twice with ethyl butan-2-one. The combined organic layers were washed with brine, dried, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (n-hexane/ethyl acetate gradient) providing 450 mg of a mixture of the desired product with its para regioisomer that eluted with the same retention time (63% UV purity). This material was used without further purification.

Provenance & Evidence