Benzyl Chloride → tert-Butyl 4-[4-(3-phenylprop-1-yn-1-yl)-1,3-thiazol-2-yl]piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Under argon, benzyl chloride (134 mg), bis(acetonitrile)dichloropalladium(II) (5.5 mg), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (30 mg) and caesium carbonate (363 mg) are added to a degassed solution of tert-butyl 4-(4-ethynyl-1,3-thiazol-2-yl)piperidine-1-carboxylate (X-1, 310 mg) in tetrahydrofuran (4 ml). The mixture is then warmed to 65° C. After subsequent cooling, the catalyst is removed by filtration over Celite and the filtrate is concentrated under reduced pressure. After chromatographic purification, this gives tert-butyl 4-[4-(3-phenylprop-1-yn-1-yl)-1,3-thiazol-2-yl]piperidine-1-carboxylate (329 mg).

Provenance & Evidence