Water → 3-Nitro-2-vinylpyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloro-3-nitropyridine (20 g, 126.15 mmol) in 1, 4 dioxane (378 mL) was added tributyl vinyl tin (48 g, 151.38 mmol). The reaction mixture was degassed using nitrogen for 30 min. Bis-(triphenylphosphin)palladium(II)-chloride (4.4 g, 6.3 mmol) was added to the reaction mixture. Reaction mass was stirred at 110° C. for overnight. The reaction mixture was cooled to rt. Water was added to the reaction mass and extracted with EtOAc. Organic layer was washed with brine and dried over Na2SO4. The organic layer was concentrated in vacuo and purified by column chromatography on silica gel using 0-5% EtOAc in hexane to give 3-nitro-2-vinylpyridine: 1H NMR (400 MHz, DMSO-d6) δ 5.741 (dd, J=2.0 Hz, J=10.4 Hz, 1H), 6.536 (dd, J=2.4 Hz, J=16.8 Hz, 1H), 7.134-7.202 (m, 1H), 7.593 (dd, J=4.4 Hz, J=8.4 Hz, 1H), 8.388 (dd, J=1.6 Hz, J=8.4 Hz, 1H), 8.857 (dd, J=0.8 Hz, J=4.4 Hz, 1H); LC-MS (ESI) m/z 151.1 [M+H]+.

Provenance & Evidence