Cesium carbonate → 5-(6-(4-fluoro-1H-indol-2-yl)-5-(2-hydroxyethyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 5-(6-chloro-5-(hydroxymethyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (300 mg, 0.58 mmol) and 4-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (197 mg, 0.75 mmol) in 1,4-dioxane (5 mL) and water (300 μL) was added Cs2CO3 (377 mg, 1.16 mmol) and 1,1′-bis(di-tert-butylphosphino)ferrocene palladium chloride (38 mg, 0.06 mmol) under N2 protection. The resulting mixture was heated to 80° C. and stirred at this temperature overnight. The reaction was cooled, filtered through a pad of celite and washed with ethyl acetate. The combined filtrate was evaporated in vacuo. Preparative TLC (eluted with 0-30% acetone/hexane) to provide 5-(6-(4-fluoro-1H-indol-2-yl)-5-(2-hydroxyethyl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (280 mg, yield: 78%) MS (M+H)+: 617.

Provenance & Evidence