Cesium carbonate → HCID 68360801, compound

Participants

Reaction Steps

2.0 g of 3,5-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline (Intermediate 1A; 64% pure, 3.25 mmol, 1 eq.), 0.98 g tert-butyl [(3-hydroxybenzyl)sulfamoyl]carbamate (Intermediate 2A; 3.24 mmol, 1 eq.) and 1.6 g caesium carbonate (4.9 mmol, 1.5 eq.) were suspended in 25 mL DMF and stirred in a closed vial at rt for 3 days. Additional 0.4 eq. tert-butyl [(3-hydroxybenzyl)sulfamoyl]carbamate and 0.4 eq. caesium carbonate were added and stirring was continued for 2 days. The reaction mixture was partitioned between sodium chloride solution and ether, the layers were separated and the aqueous layer was reextracted with ether. The combined organic layers were dried, filtered and concentrated in vacuo to yield 3.08 g of the crude product (as a regioisomeric mixture containing some unreacted starting material), which was used in the subsequent reaction without further purification.

Provenance & Evidence