Water → 1'-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,5-triazin-2-yl]-1,4'-bipiperidinyl-3-ol

Participants

Reaction Conditions

Reaction Steps

45 mg (0.42 mmol) of sodium carbonate are added to 50 mg (0.17 mmol) of 1′-(4-chloro-1,3,5-triazin-2-yl)-1,4′-bipiperidinyl-3-ol and 139 mg (0.42 mmol) of 4,4,5,5-tetramethyl-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,2-dioxaborolane in 3.2 ml of toluene/ethanol/water (3.2/3.2/1). The reaction mixture is degassed a number of times, and 19 mg (0.017 mmol) of tetrakis-(triphenylphosphine)palladium(0) are added under nitrogen atmosphere, the mixture is treated in an ultrasound bath for 10 min and subsequently heated at 90° C. for 5 h. Water is added to the reaction mixture, which is then extracted three times with ethyl acetate/ether. The combined organic phases are dried over Na2SO4 and evaporated. The crude product is purified by means of preparative HPLC.

Provenance & Evidence