Nitrogen → N-(2-bromopyridin-4-yl)-2,6-dichloro-4-vinylbenzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(2-bromopyridin-4-yl)-2,6-dichloro-4-iodobenzamide (3.0 g, 6.4 mmol) in THF (40 mL) was added 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (2.0 g, 12.8 mmol), 2M Na2CO3 (12 ml) and Pd2(PPh3)4 (222 mg, 0.19 mmol). The solution was degrassed with N2, and heated at 80° C. overnight. Then the reaction mixture was cooled to room temperature, poured into water (200 mL), and extracted with EtOAc (3×100 mL). The combined organic extracts were washed with brine (2×20 mL), dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica-gel chromatography (Pet Ether/EtOAc=10:1 to 3:1) to give N-(2-bromopyridin-4-yl)-2,6-dichloro-4-vinylbenzamide (2.2 g, yield: 92%). 1H NMR (500 MHz, CDCl3): δ 8.27 (d, J=5.0 Hz, 1H), 8.11 (s, 1H), 7.88 (s, 1H), 7.51 (d, J=3.5 Hz, 1H), 7.35 (s, 2H), 6.61 (m, 1H), 5.86 (d, J=17.5 Hz, 1H), 5.48 (d, J=11.0 Hz, 1H). LCMS (ESI) m/z: 371.0 [M+H+].

Provenance & Evidence