(2-Methylpropyl)boronic acid → HCID 86684978, compound

Participants

Reaction Steps

5,7-dichloro-2-(3,5-dimethylphenyl)quinoline (4.8 g, 15.9 mmol), isobutylboronic acid (6.48 g, 63.5 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (1.04 g, 2.54 mmol), Pd2(dba)3 (0.582 g, 0.635 mmol), potassium phosphate monohydrate (36.6 g, 159 mmol) and 2 mL of water were mixed in 240 mL of toluene. The system was degassed with nitrogen for 20 minutes and refluxed overnight. After cooling to room temperature, the reaction mixture was filtered through a Celite® plug and eluted with dichloromethane. The product was purified by column chromatography (4:1 to 1:1 hexanes/ethyl acetate, v/v) to give 5.2 g (41% yield) of 2-(3,5-dimethylphenyl)-5,7-diisobutylquinoline, which was confirmed by GCMS.

Provenance & Evidence