反应详情

温度

80 °C

A mixture of 3,6-dichloropyridazine (6 g, 40.3 mmol), vinyl boronic acid pinacol ester (6.21 g, 6.83 mL, 40.3 mmol), potassium carbonate (120 mmol, 16.7 g), 1,4-dioxane (60 mL) and water (24 mL) was degassed for 15 min with nitrogen gas. Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.4 mmol, 292 mg) was then added and the mixture heated to 80° C. for 4 hours. The aqueous phase was then removed via pipette and the organic phase concentrated onto silica gel and purified via flash column chromatography (SiO2, hexane:ethyl acetate 100:0-60:40) to return 3-chloro-6-vinyl-pyridazine as a white solid (5.2 g, 92% yield). 1H NMR (CDCl3) δ 5.75 (1H, d), 6.25 (1H, d), 7.05 (1H, dd), 7.49 (1H, d), 7.59 (1H, d). MS m/z=141 (M+H+)+.

1. customwas degassed for 15 min with nitrogen gas
2. customThe aqueous phase was then removed via pipette
3. concentrationthe organic phase concentrated onto silica gel
4. custompurified via flash column chromatography (SiO2, hexane:ethyl acetate 100:0-60:40)