Iodine → HCID 15702077, compound

Participants

Reaction Conditions

Reaction Steps

0.1 m of n-BuLi (1,5 M in hexane) is added dropwise to a solution of 0.1 m of 1-[p-(5-n-propyl-2-pyrimidinyl)-phenyl]-2-(3,5-difluorophenyl)ethane (prepared in accordance with scheme 1) and 0.1 m of TMEDA in 300 ml of THF at approximately -90° . Stirring is carried out for a further 30 min at this temperature and then a solution of 0.1 m of I2 in 70 ml of THF is slowly added. After addition is complete, the solution is allowed to heat up to -20° and hydrolyzation is carried out with H2O. The product is completely dissolved by adding diethyl ether and excess I2 is removed by washing with sodium thiosulfate solution and H2O. After evaporating down, the product is left behind as a residue and without further purification, is heated with 0.12 m of (CuCN)x and 100 ml of NMP for 4 h at 170° C. in an oil bath. After this time, water and CH2CH2 are added to the cooled reaction mixture, and the organic phase is washed, dried and evaporated down. The pure product can be obtained by chromatography and crystallization. 1-[p-(5-n-propyl-2-pyrimidinyl)-phenyl]-2-(4-cyano-3,5difluorophenyl)ethane is obtained.

Provenance & Evidence