Cesium carbonate → HCID 68360870, compound

Participants

Reaction Steps

3.0 g of 3,5-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline (Intermediate 1A; 70% pure, 5.3 mmol, 1 eq.), 1.1 g N-Boc-3-amino-phenol (5.3 mmol, 1 eq.) and 3.4 g caesium carbonate (10.7 mmol, 1.5 eq.) were suspended in 30 mL DMF and stirred at rt for 16 h. LCMS analysis showed complete turnover. The reaction mixture was partitioned between water and ethyl acetate, the layers were separated and the aqueous layer was reextracted with ethyl acetate. The combined organic layers were dried, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (n-hexane/ethyl acetate gradient) providing 1.35 of the desired product (44% yield).

Provenance & Evidence