6-Bromoquinoline → HCID 68083972, compound

Participants

Reaction Steps

In a stream of argon, 0.34 g (1.62 mmol) of 6-bromoquinoline was dissolved in 7 mL of tetrahydrofuran, and then 1.03 mL of a solution of butyllithium 1.63 mmol in hexane was added dropwise at −78° C. The resultant mixture was stirred at −78° C. for 30 minutes, and then 0.41 g (1.63 mmol) of dichloro(tetramethylethylenediamine)zinc was added. The mixture was heated to room temperature and maintained at that temperature for 1 hour while being stirred. To the resultant mixture, 0.20 g (0.41 mmol) of 2-(3,5-dibromophenyl)-4,6-di-p-tolylpyrimidine, 19 mg (0.016 mmol) of tetrakis(triphenylphosphine)palladium and 3 mL of tetrahydrofuran were added, and the obtained suspension was heated under reflux for 17 hours. The reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove all volatile materials. The thus-deposited solid was collected by filtration. The thus-obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:1) mixed solvent as an eluent to give 0.16 g of the target 2-[3,5-di(6-quinolyl)phenyl-4,6-di-p-tolylpyrimidine as a white solid (yield: 65%).

Provenance & Evidence