2-Chloropyridine → HCID 67382629, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-azabicyclo[2.2.2]octan-3-one (0.6 g, 4.8 mmol), 2-chloropyridine (0.65 g, 5.76 mmol), Cs2CO3 (2.36 g, 7.20 mmol) and xantphos (0.22 g, 0.38 mmol) in 1,4-dioxane (30 ml) was purged with argon gas for 15 min. Tetrakis(triphenylphosphine)palladium (0) (0.22 g, 0.19 mmol) was added and continued purging for another 10 min. The reaction mixture was heated at 125° C. for 3 h. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated and dried under reduced pressure to afford the crude compound. Purification by column chromatography over neutral alumina using 15% ethyl acetate in petroleum ether as eluent afforded 600 mg (61.9%) of 2-(pyridin-2-yl)-2-aza-bicyclo[2.2.2]octan-3-one as pale yellow solid.

Provenance & Evidence