Benzyl mercaptan → 3-(Benzylthio)-8-chloro-1,7-naphthyridine

Participants

Reaction Conditions

Reaction Steps

To a vial charged with 3-bromo-8-chloro-1,7-naphthyridine (Anichem, North Brunswick, N.J.) (360 mg, 1.479 mmol) was added dioxane (5914 μl), DIEA (516 μl, 2.96 mmol), Xantphos (171 mg, 0.296 mmol), Pd2(dba)3 (135 mg, 0.148 mmol) and benzyl mercaptan (184 μl, 1.552 mmol). The vessel was sealed and heated to 40° C. overnight. The mixture was cooled to RT, filtered through diatomaceous earth and dried under reduced pressure. The crude residue was purified with a 25 g silicycle HP column (25 μm spherical silica) ramping EtOAc in heptane (0 to 100%, 10% DCM throughout) to provide 3-(benzylthio)-8-chloro-1,7-naphthyridine (0.218 g, 0.760 mmol, 51.4% yield) as a light yellow solid. m/z (ESI) 287.1 (M+H)+.

Provenance & Evidence