1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 5-(4-(2-(t-Butyldimethylsilyloxy)ethyl)piperidin-1-yl)-2-chloropyridine

Participants

Reaction Conditions

Reaction Steps

2-chloro-5-iodopyridine (1.00 g, 4.18 mmol), compound 292 (1.02 g, 4.18 mmol), Tris(dibenzylideneacetone)dipalladium (0) (0.191 g, 0.209 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene (0.242 g, 0.418 mmol), and sodium t-butoxide (0.803 g, 8.35 mmol) were dissolved in 20 mL dioxane. The reaction was purged with argon and heated at 80° C. for 16 hours. The solvent was removed in vacuo and silica gel chromatography (gradient elution hexanes/0-10% ethyl acetate) afforded compound 293 as a beige solid (597 mg, 40%).

Provenance & Evidence