Potassium Carbonate → HCID 25918949, compound

Participants

Reaction Steps

Bromine was added to a solution of 4-(4-fluoro-phenyl)-thiazol-2-ylamine (12 g, 62 mmol) in acetic acid at room temperature. The mixture was stirred at room temperature for 30 sec and solidified. The mixture was diluted with water and poured to ice-water. The light grey suspension was filtered. The solid obtained was taken up in EtOAc and carefully basified with aqueous K2CO3 (pH was adjusted to 8˜9). The EtOAc extract was dried over MgSO4 and concentrated to give crude 5-bromo-4-(4-fluoro-phenyl)-thiazol-2-ylamine (15.15 g). This was then mixed with 4-fluorophenol (6.9 g, 62 mmol) and Cs2CO3 (22 g, 68 mmol) in acetonitrile (120 mL) and heated at 70° C. for 2 h and concentrated. The residue was partitioned between EtOAc and water. The organic extract was dried over MgSO4, concentrated and chromatographed to give the title compound with some impurities. m/z 305.1 (MH+).

Provenance & Evidence