Benzyl mercaptan → (E)-ethyl 3-(5-(benzylthio)-2-chloropyridin-3-yl)acrylate

Participants

Reaction Conditions

Reaction Steps

A vial was charged with (E)-ethyl 3-(5-bromo-2-chloropyridin-3-yl)acrylate (660 mg, 2.272 mmol), phenylmethanethiol (296 mg, 2.385 mmol), Xantphos (131 mg, 0.227 mmol), Pd2(dba)3 (104 mg, 0.114 mmol), 1,4-dioxane (9086 μl), and Hunig's base (793 μl, 4.54 mmol). The vial was purged with argon and the mixture was heated at 80° C. for 1 h. Water and EtOAc were added, and the layers were separated. The organic portion was dried, filtered and concentrated. The crude material was purified by silica gel chromatography, 0-50% EtOAc/heptane to provide (E)-ethyl 3-(5-(benzylthio)-2-chloropyridin-3-yl)acrylate (790 mg, 2.366 mmol, 104% yield) as a yellow oil. m/z (ESI) 334.0 (M+H)+.

Provenance & Evidence