Potassium Carbonate → 5-(5-(2-(benzyloxy)-1-fluoroethyl)-6-chloropyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (714 mg, 1.422 mmol) and 3-(2-(benzyloxy)-1-fluoroethyl)-6-bromo-2-chloropyridine (490 mg, 1.422 mmol) in 1,4-Dioxane (15 ml) and water (2 mL) was added K2CO3 (393 mg, 2.84 mmol) and Pd(dppf)Cl2 (100 mg, 0.137 mmol) under N2 protection. The resulting mixture was heated to 85° C. and stirred for 6 h. The reaction was cooled, filtered through a pad of celite and washed with ethyl acetate. The combined filtrate was evaporated in vacuo. The resulting residue was purified using column chromatography (eluted with 0-20% ethyl acetate/DCM) to provide 5-(5-(2-(benzyloxy)-1-fluoroethyl)-6-chloropyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (660 mg, yield: 67%). MS (M+H)+: 641.

Provenance & Evidence