反应详情

温度

85 °C

A solution of 5-chloro-6-ethyl-pyridin-3-yl-acetonitrile (3.00 g, 16.6 mmol) and allyl-tri-n-butyltin (5.4 mL, 17.4 mmol) in acetonitrile (30 mL, 0.5 M) and dimethylsulfoxide (2 mL), is degassed and treated with 1,1′-bis(diphenylphosphino)ferrocene-dicloronickel(II) (Ni(dppf)Cl2) (0.38 g, 0.55 mmol). The mixture is warmed to 85° C. for 2 h. After cooling to room temperature the solution is diluted with 10% aq potassium fluoride (30 mL) and ethyl acetate (30 mL). The solids are filtered and rinsed with ethyl acetate (30 mL). The organic layer is washed with saturated aq NaCl (80 mL) and dried over Na2SO4. The product is purified by MPLC (25-90% ethyl acetate in n-heptane) to provide 5-allyl-6-ethyl-pyridin-3-yl-acetonitrile as a yellow oil (2.43 g, 79%): Rf 0.28 (50% ethyl acetate in n-heptane), 1H NMR (CDCl3, 300 MHz) δ 8.36 (s, 1 H), 7.44 (s, 1 H), 6.00-5.84 (m, 1 H), 5.15 (d, J=10.3 Hz, 1 H), 5.03 (d, J=17.2 Hz, 1 H), 3.71 (s, 2 H), 3.42 (d, J=6.0 Hz, 2 H), 2.83 (q, J=7.6 Hz, 2 H), 1.28 (t, J=7.6 Hz, 3 H). ESI-LCMS m/z calcd for C12H14N2: 186.1; found 187.0 (M+1)+.

1. temperatureAfter cooling to room temperature the solution
2. filtrationThe solids are filtered
3. washrinsed with ethyl acetate (30 mL)
4. washThe organic layer is washed with saturated aq NaCl (80 mL)
5. dry with materialdried over Na2SO4
6. customThe product is purified by MPLC (25-90% ethyl acetate in n-heptane)