Cesium carbonate → HCID 117746867, compound

Participants

Reaction Conditions

Reaction Steps

A RBF was charged with (E)-ethyl 3-(2-amino-5-(benzylthio)phenyl)acrylate (625 mg, 1.994 mmol, made via Method 42, Steps 1-2), 2-bromo-5-iodo-4-methoxybenzonitrile (809 mg, 2.393 mmol), Xantphos (57.7 mg, 0.100 mmol), Pd2(dba)3 (45.7 mg, 0.050 mmol), and cesium carbonate (1624 mg, 4.99 mmol) were added. A reflux condenser was attached, and the flask was heated to 110° C. overnight. The mixture was cooled, diluted with EtOAc, and filtered through celite with the aid of EtOAc. The filtrate was concentrated. The residue was taken up in 2-PrOH, and the mixture was heated to boiling briefly then sonicated for 30 s. When the mixture had returned to room temperature, it was filtered; and the filtered solid was washed with 2-PrOH (3×). The collected solid was dried on the filter under a flow of N2 (g) for 15 min to give (E)-ethyl 3-(5-(benzylthio)-2-((4-bromo-5-cyano-2-methoxyphenyl)amino)phenyl)acrylate (963 mg, 1.840 mmol, 92% yield) as a bright-yellow solid. m/z (ESI) 545.0 (M+Na)+.

Provenance & Evidence