4-Methoxypiperidine → HCID 59327226, compound

Participants

Reaction Conditions

Reaction Steps

A round-bottomed flask was charged with 3-bromo-2-chloropyridine (620 mg, 3.22 mmol), 4-methoxy-piperidine (371 mg, 3.22 mmol), tris(dibenzylideneacetone)dipalladium(0) (147 mg, 0.161 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (186 mg, 0.322 mmol), and sodium tert-butoxide (464 mg, 4.83 mmol) in toluene (6442 μL), sealed and then sparged with argon for 5 min. The reaction mixture was heated at 100° C. with stirring for 2 h. After cooling to RT, the reaction mixture was filtered through a pad of celite and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 0% to 40% EtOAc in hexane, to provide 2-chloro-3-(4-methoxypiperidin-1-yl) as orange oil. MS (ESI, pos. ion) m/z: 226.8 (M+1).

Provenance & Evidence