Dichloromethane → N-[5-(6-Chloro-5-methylsulfonyl-pyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide

Participants

Reaction Steps

A solution of 5-bromo-2-chloro-3-methylsulfonylpyridine (0.135 g, 0.5 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) 1:1 complex with dichloromethane (24 mg, 0.03 mmol), bis(pinacolato)diboron (0.135 g, 0.53 mmol) and potassium acetate (0.147 g, 1.5 mmol) in 1,4-dioxane (4 mL) was heated at 80° C. for 18 hours. The reaction mixture was cooled and N-(5-iodo-4-methyl-1,3-thiazol-2-yl)acetamide (100 mg, 0.35 mmol), 2M aqueous sodium carbonate (1.25 mL, 2.5 mmol), ethanol (0.6 mL) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) 1:1 complex with dichloromethane (12 mg, 0.015 mmol) were added. The resultant mixture was heated again at 80° C. for 8 hours. The resultant mixture was filtered through a plug of celite and purified with preparative HPLC (Method A) to give the title compound (30 mg, 17%; retention time

Provenance & Evidence