Cesium carbonate → Tert-butyl [3-({4-carbamoyl-5-[(2-fluoro-4-iodophenyl)amino]pyridin-3-yl}oxy)phenyl]carbamate

Participants

Reaction Steps

31 mg of 3-fluoro-5-[(2-fluoro-4-iodophenyl)amino]isonicotinamide (0.083 mmol, 1. eq.) and 17 mg of tert-butyl (3-hydroxyphenyl)carbamate (0.083 mmol, 1 eq.) were dissolved in 1 ml of DMF, then 81 mg of cesium carbonate (0.248 mmol, 3 eq.) were added. The resulting mixture was stirred at room temperature for 18 hours. Since the reaction was not complete, the mixture was stirred for another 3 days at 50° C. bath temperature. The mixture was then partitioned between aq. NH4Cl solution (10 ml) and dichloromethane (10 ml). The phases were separated and the aqueouse layer was reextracted twice with dichloromethane (10 ml each). The combined organic layers were washed with brine (20 ml), dried over a silicone filter and concentrated in vacuo. The residue was purified by flash chromatography to yield 17 mg (0.03 mmol, 30%) of the analytically pure target compound.

Provenance & Evidence