8-Hydroxyquinoline → 1-(2-(4-ethoxyphenyl)thiazol-5-yl)-3,5-dimethylpyridin-2(1H)-one

Participants

Reaction Steps

A mixture of CuI (0.038 g, 0.20 mmol), Cs2CO3 (0.98 g, 3.00 mmol) and 8-hydroxyquinoline ligand (0.029 g, 0.20 mmol) in DMSO (2 mL) was stirred at rt for 30 min under N2. Then to the reaction mixture was added a solution of 3,5-dimethylpyridin-2(1H)-one (0.30 g, 2.40 mmol) and 5-bromo-2-(4-ethoxyphenyl)thiazole (0.57 g, 2.00 mmol) in DMSO (2 mL) via syringe. The reaction mixture was heated at 130° C. for 12 h, then cooled to rt and filtered. The filtrate was diluted with H2O (10 mL) and extracted with CH2Cl2 (20 mL×3). The combined organic phases were concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:10) to give the title compound (0.17 g, 26%). The compound was characterized by the following spectroscopic data:

Provenance & Evidence