Piperidine → 6-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-4-methyl-2-(4-methylpiperidin-1-yl)quinoline

Participants

Reaction Steps

A solution of 293 mg (0.8 mmol) of 6-iodo-4-methyl-2-(4-methylpiperidin-1-yl)quinoline, 184 mg (0.8 mmol, 93% purity) 5-(4-chlorophenyl)-2-ethynylpyridine, and 158 μL (1.6 mmol) of piperidine in 4 mL of 1,4-dioxane is evacuated three times and gassed with argon. After the addition of 3 mg (0.016 mmol) of CuI and 13 mg (0.016 mmol) of PdCl2(dppf)-DCM complex, the reaction mixture is stirred for 4 hours at RT. It is combined with 10 mL of EtOAc, and the precipitate is filtered off, washed with a little EtOAc and MeOH, and dried in the air. Yield: 240 mg (66% of theoretical); C29H26ClN3 (M=451.990); calc.: molpeak (M+H)+: 452/454 (Cl); found: molpeak (M+H)+: 452/454 (Cl); HPLC-MS: 6.1 min (method B).

Provenance & Evidence