Description
(2E)-3-(Dimethylamino)-1-(3-pyridyl)prop-2-en-1-one is a pharmaceutical intermediate used as an intermediate of nilotinib, a targeted anticancer drug for the treatment of chronic myeloid leukaemia (CML).
Synthesis
Example-2: Preparation of 3-dimethylamino-1-pyridin-3-ylacrylone
Method A: 3-Acetylpyridine (25 g, 0.20 mol), N,N-dimethylformamide dimethyl acetal (37 g, 0.31 mol) and acetic acid (2.5 ml) were mixed and the reaction was heated at 90-95°C for 2 hours, during which time the methanol produced was continuously removed. After completion of the reaction, excess methanol in the reaction was removed by distillation under reduced pressure. The reaction mixture was diluted with water and extracted with dichloromethane (125 ml). The organic layer was washed with water and the solvent was removed by distillation under reduced pressure to afford 34 g (92% yield) of (E)-3-(dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one with a purity of 99.1% by HPLC analysis.
References
[1] Synlett, 2016, vol. 27, # 15, p. 2233 - 2236
[2] RSC Advances, 2018, vol. 8, # 47, p. 26828 - 26836
[3] Molecules, 2009, vol. 14, # 10, p. 4166 - 4179
[4] Patent: WO2011/39782, 2011, A1. Location in patent: Page/Page column 14
[5] Organic Process Research and Development, 2008, vol. 12, # 3, p. 490 - 495
