2,4-Dichloro-6-(4-isopropoxyphenyl)pyridine → 2-(4-Chloro-6-(4-isopropoxyphenyl)pyridin-2-yl)thiazole

Participants

Reaction Steps

To a dry 2 dram vial equipped with a stir bar was added 2,4-dichloro-6-(4-isopropoxyphenyl)pyridine (60 mg, 0.21 mmol) and Pd(dppf)Cl2 (8 mg, 10 μmol). The vial was sealed with a septum screw-cap and was then placed under N2 atmosphere. To the vial was added THF (0.5 mL), then thiazol-2-ylzinc(II) bromide in THF (0.5M, 0.53 mL, 0.27 mmol). The vial was placed in a 60° C. heating block with stirring for 2 hours. The vial was opened, and then charged with Pd(dppf)Cl2 (8 mg, 10 μmol). The vial was re-sealed and then placed under N2 atmosphere, and to the vial was added thiazol-2-ylzinc(II) bromide in THF (0.5M, 0.53 mL, 0.27 mmol). The vial was placed in a 60° C. heating block with stirring for 5 hours. The reaction solution was cooled to room temperature and then concentrated under a stream of N2. The resulting solid residue was subjected to silica gel chromatography to afford 2-(4-chloro-6-(4-isopropoxyphenyl)pyridin-2-yl)thiazole as a white solid (24 mg, 34%).

Provenance & Evidence