Potassium Carbonate → HCID 10022197, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-[(3-chloro-2-pyridyl)amino]-1,3-thiazole-4-carboxylate. A mixture of ethyl 2-amino-1,3-thiazole-4-carboxylate (2.33 g, 13.5 mmol), 2,3-dichloro-pyridine (2.0 g, 13.5 mmol, Lancaster), palladium (II) acetate (152 mg, 0.68 mmol, Strem Chemicals), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (420 mg, 0.68 mmol, Aldrich), potassium carbonate (37.3 g, Mallinckrodt) and toluene (55 mL) in a sealed flask was stirred at 112° C. under N2 for 2 d. The reaction mixture was passed through a pad of Celite and the Celite pad was washed with EtOAc (5×100 mL). The organic layer was diluted with H2O (200 mL), and separated from the aqueous phase. The aqueous phase was extracted with EtOAc (150 mL). The combined organic phase was washed with satd NaCl (200 mL), dried over Na2SO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (0-15% EtOAc in hexane) provided the title compound as a white solid. MS (ESI, pos. ion) m/z: 284 (M+1).

Provenance & Evidence