Potassium Phosphate, Tribasic → 5-(4-(4-fluoro-1H-indol-2-yl)-5-vinylpyrimidin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 2-(2-chloro-5-vinylpyrimidin-4-yl)-4-fluoro-1H-indole (100 mg, 0.36 mmol) and (2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethyl sulfonamido)benzofuran-5-yl)boronic acid (150 mg, 0.36 mmol) in 1,4-dioxane (5 mL), Pd2(dba)3 (20 mg), X-Phos (20 mg) and K3PO4 (200 mg, 0.56 mmol) were added under N2. The mixture was heated to 80° C. for 2 hours. The reaction mixture was cooled to RT, filtered and washed with EtOAc. The filtrate was washed with H2O, brine, and dried over Na2SO4. After concentration, the residue was purified by column chromatography (DCM:MeOH 40:1) to give the product of 5-(4-(4-fluoro-1H-indol-2-yl)-5-vinylpyrimidin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (150 mg, yield: 68.4%). 1H-NMR (CDCl3, 400 MHz) δ 10.76 (br s, 1H), 8.88 (s, 1H), 8.63 (s, 1H), 7.98˜8.05 (m, 2H), 7.64 (s, 1H), 7.59 (s, 1H), 7.15˜7.25 (m, 6H), 6.74˜6.84 (m, 1H), 5.91 (d, J=18.0 Hz, 1H), 5.69 (d, J=11.2 Hz, 1H), 3.39 (s, 3H), 3.03 (d, J=4.8 Hz, 3H), 2.87 (s, 3H). MS (M+H)+: 614

Provenance & Evidence