Synthesis
1. Synthesis of 2-vinylquinoline (1-2): 2-Chloroquinoline (1-1) (1.00 g, 6.1 mmol) was dissolved in toluene (25 mL) and sprayed with N2 gas for 5 min to deoxidize. Subsequently tributyl (vinyl) stannane (2.52 g, 8.0 mmol) and tetrakis (triphenylphosphine) palladium (0.353 g, 0.31 mmol) were added. The reaction mixture was heated at 125 °C for 1 h. After completion of the reaction it was cooled to room temperature and concentrated under vacuum. The concentrated residue was suspended in dichloromethane (20 mL) and purified by silica gel fast column chromatography (80 g silica gel column) with an elution gradient of 0-30% ethyl acetate/hexanes and an elution time of 20-30 min. Fractions containing the target product 2-vinylquinoline (1-2) were collected, combined and the solvent was removed under vacuum to give 700 mg (74% yield) of a clear, oily product. LC/MS analysis showed m/z (M + H) = 156.0.
References
[1] Patent: WO2013/28590, 2013, A1. Location in patent: Page/Page column 33; 34
[2] Patent: EP2714041, 2016, B1. Location in patent: Paragraph 0111
[3] Patent: WO2013/74390, 2013, A1. Location in patent: Page/Page column 34
[4] Organic Letters, 2000, vol. 2, # 4, p. 433 - 436
[5] Patent: EP2621926, 2017, B1
