4-Pyridinecarbonitrile,2-ethenyl-(9CI) synthesis
- Product Name:4-Pyridinecarbonitrile,2-ethenyl-(9CI)
- CAS Number:98436-74-9
- Molecular formula:C8H6N2
- Molecular Weight:130.15
Yield:98436-74-9 58%
Reaction Conditions:
with tetrakis(triphenylphosphine) palladium(0);lithium chloride in tetrahydrofuran at 110; for 12 h;Inert atmosphere;Sealed tube;Stille Cross Coupling;
Steps:
Synthesis of 3-vinylbenzonitrile (3b)
General procedure: To a solution of Pd(PPh3)4 (480 mg, 5 mol%) and LiCl (420 mg, 9.91 mmol, 1.2 eq.) in anhydrous THF (30 mL), 3-bromobenzonitrile (1.5 g, 8.33 mmol, 1.0 eq.) and tributyl(vinyl)tin (3.8 g, 11.99 mmol, 1.44 eq.) were added under Ar atmosphere and stirred in a closed-seal reactor at 110 °C for 12 h. The reaction mixture was evaporated and purified with column chromatography using a linear gradient of petroleum ether and diethyl ether 10:1 to 5:1.
References:
Hrast, Martina;Frlan, Rok;Knez, Damijan;Zdovc, Irena;Barreteau, Hélène;Gobec, Stanislav [Bioorganic and Medicinal Chemistry Letters,2021,vol. 40,art. no. 127966] Location in patent:supporting information
