Benzyl mercaptan → HCID 178516457, compound

Participants

Reaction Conditions

Reaction Steps

A screw cap vial was charged with 7-chloro-1,6-naphthyridin-4-ol (0.500 g, 2.77 mmol), Xantphos (0.080 g, 0.138 mmol), tris(dibenzylideneacetone)dipalladium (0.063 g, 0.069 mmol), 1,4-dioxane (5.54 mL) and DIPEA (0.963 mL, 5.54 mmol). The vial was purged with argon, sealed and heated to 80° C. for 10 minutes. The reaction was cooled to room temperature and benzyl mercaptan (0.385 mL, 3.25 mmol) was added and the reaction was continued heating at 80° C. for an additional 30 minutes. The reaction was cooled to room temperature, diluted with water and extracted with DCM (3×). The combined organics were washed with water and brine, dried over magnesium sulfate, filtered and concentrated. The resulting material was concentrated, dissolved in minimal DCM and purified via column chromatography (silica gel 40 g, gradient elution 0 to 50% EtOAc:Heptane) to afford 0.168 g of 7-(benzylthio)-1,6-naphthyridin-4-ol. m/z (ESI) 269.1 (M+H)+.

Provenance & Evidence