2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide → HCID 77845572, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 2-chloro-11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridine (50 mg, 0.18 mmol) and 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (120 mg, 0.24 mmol) in 1,4-dioxane (8 mL) and water (200 μl) was added CS2CO3 (119 mg, 0.37 mmol) and 1,1′-bis(di-tert-butylphosphino)ferrocene palladium chloride (20 mg, 0.03 mmol) under N2 protection. The resulting mixture was heated to 90° C. and stirred for 4 hours. The reaction was cooled, filtered through a pad of the celite and washed with ethyl acetate. The combined filtrate was evaporated in vacuo. Preparative TLC (eluted with 30% EtOAc/DCM) provide 5-(11-fluoro-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (90 mg, yield: 80%) MS (M+H)+: 613.

Provenance & Evidence