Cesium carbonate → HCID 58541696, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6-(4-fluorophenyl)-imidazo[2,1-b]thiazole (J) (6.0 g, 27.6 mmol), 4-iodo-2-thiomethylpyrimidine (10.4 g, 41.3 mmol), cesium carbonate (13.4 g, 41.3 mmol), triphenylphosphine (2.88 g, 11 mmol), and palladium acetate (1.22 g, 5.5 mmol) is added anhydrous dimethylformamide (60 mL). The reaction mixture is sealed and shaken at 80° C. for 12 hours. The reaction was quenched by addition of water (200 mL). The aqueous layer is extracted with ethyl acetate (3×100 mL). The organic phase is washed sequentially with water (100 mL) and a saturated aqueous, sodium chloride solution (100 mL). The organic phase is dried over sodium sulfate, filtered, and the solvent evaporated in vacuo. The crude product is purified by silica gel column chromatography, eluting with a gradient of ethyl acetate/hexane (20-30%). After evaporation of the solvent, 6-(4-fluorophenyl)-5-(2-methylsulfanyl-pyrimidin-4-yl)-imidazo[2,1-b]thiazole (K) (Compound CXXXIX, Table 2) is obtained as a white solid (3.5 g, 37%) m.p. 151-152° C.;

Provenance & Evidence