Cesium carbonate → (E)-6-bromo-2-chloro-3-(2-ethoxyvinyl)pyridine

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6-bromo-2-chloro-3-iodopyridine (8.0 g, 25.1 mmol), (E)-2-(2-ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.98 g, 25.1 mmol), cesium carbonate (16.38 g, 50.3 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (2.052, 2.51 mmol) was added 1,4-dioxane (100 mL) and H2O (10 mL). A steady stream of N2 was bubbled through the reaction mixture for 15 minutes then the mixture was heated to 73° C. for 20 h. The mixture was cooled to ambient temperature, diluted with EtOAc, and washed successively with H2O (2×) and brine (1×). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography using a step gradient of 0-10-60% EtOAc/Hexanes as eluent. MS (M+H): 261.

Provenance & Evidence