p-Toluenesulfonic acid → 6-(4-Chloro-phenyl)-2-(4-pyrrolidin-1-ylmethyl-phenylethynyl)-quinoline

Participants

Reaction Steps

3 mg p-toluenesulphonic acid and 100 μL glacial acetic acid are added to a solution of 290 mg (0.78 mmol) 4-[6-(4-chloro-phenyl)-quinoline-2-ylethynyl]-benzaldehyde and 56 mg (0.78 mmol) pyrrolidine in 10 mL THF at RT and stirred for 30 minutes. Then 334 mg (1.57 mmol) NaBH(OAc)3 are added batchwise and the reaction mixture is stirred for 14 h. A few drops of water are added dropwise to the reaction mixture and this is stirred for 15 minutes. The reaction mixture is then combined with K2CO3 and filtered. The filtrate is evaporated down. The purification is carried out by column chromatography on silica gel (DCM/MeOH/NH3 90:10:1).

Provenance & Evidence