2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → 5-(5-(benzyloxy)-6-(4-fluoro-1H-indol-2-yl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3-(benzyloxy)-6-chloropyridin-2-yl)-4-fluoro-1H-indole (160 mg, 0.454 mmol), 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (228 mg, 0.454 mmol), K3PO4.H2O (362 mg, 1.362 mmol), Pd2(dba)3 (21 mg, 0.023 mmol) and X-Phos (22 mg, 0.046 mmol) in dioxane/H2O (2 mL/0.4 mL) was stirred at 80° C. for 2 hours under N2 atmosphere. The mixture was then diluted with water (50 mL) and extracted with ethyl acetate (30 mL×3). The organic layer was washed with brine (20 mL×3), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using Prep-TLC (petroleum ether:EA=1:1) to provide 5-(5-(benzyloxy)-6-(4-fluoro-1H-indol-2-yl)pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (120 mg, yield: 38.2%). 1H-NMR (CDCl3, 400 MHz) δ 9.97 (s, 1H), 7.93 (s, 1H), 7.88˜7.91 (m, 2H), 7.55 (s, 1H), 7.33˜7.48 (m, 7H), 6.69˜7.19 (m, 5H), 6.65˜6.69 (m, 1H), 5.83 (d, J=4.4 Hz, 1H), 5.31 (s, 2H), 3.08 (s, 3H), 2.91 (d, J=4.8 Hz, 3H), 2.75 (s, 3H). MS (M+H)+: 693.

Provenance & Evidence