Water → benzyl 2-oxo-1-{[2-(trimethylsilyl)ethoxy]methyl}-2,2',3,3'-tetrahydro-1H,1'H-spiro[1,8-naphthyridine-4,4'-pyridine]-1'-carboxylate

Participants

Reaction Conditions

Reaction Steps

Bis(tri-t-butylphosphine) palladium(0) (9.0 mg, 0.018 mmol) was added to solution of benzyl 4-[2-((3-bromopyridin-2-yl){[2-(trimethylsilyl)ethoxy]methyl}amino)-2-oxoethyl]-3,6-dihydropyridine-1(2H)-carboxylate (0.10 g, 0.18 mmol) and dicyclohexylmethylamine (42 μL, 0.196 mmol) in dioxane (2 mL). After 5 min, the reaction mixture was heated to 50° C. After 1.5 h, additional bis(tri-t-butylphosphine) palladium(0) (9.0 mg, 0.018 mmol) was added. After 20 min, water was added and the mixture was extracted with ether (2×). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (95% hexanes/ethyl acetate→40% hexanes/ethyl acetate) gave the title compound (68 mg). MS 480.2 (M+1).

Provenance & Evidence