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

Temperature

73 °C

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.

1. customA steady stream of N2 was bubbled through the reaction mixture for 15 minutes
2. temperatureThe mixture was cooled to ambient temperature
3. additiondiluted with EtOAc
4. washwashed successively with H2O (2×) and brine (1×)
5. dry with materialThe organic layer was dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. customThe residue was purified by silica gel column chromatography

ORD record

ord-53c2e35f76284baaaa153920394e4e36

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09243002B2