Cesium carbonate → 3-chloro-2-methoxy-6-[(E)-1-[4-(propan-2-yl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethenyl]pyridine

Participants

Reaction Conditions

Reaction Steps

4-Isopropylphenylboronic acid (103 mg), tris(dibenzylideneacetone)dipalladium (38 mg), tri(2-furyl)phosphine (58 mg), cesium carbonate (273 mg) and water (0.5 mL) were added to a solution of 6-[(Z)-1-bromo-2-(tetrahydro-2H-pyran-4-yl)ethenyl]-3-chloro-2-methoxypyridine (140 mg) in 1,4-dioxane (3 mL), and the mixture was stirred at 90° C. for two hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→1:1) to give 3-chloro-2-methoxy-6-[(E)-1-[4-(propan-2-yl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethenyl]pyridine containing impurities as a yellow oil (170 mg).

Provenance & Evidence