2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl → 5-(6-(4-fluorobenzyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Participants

Reaction Steps

A solution of 2-chloro-6-(4-fluorobenzyl)-5H-pyrrolo[3,4-b]pyridin-7(6H)-one (70 mg, 0.25 mmol), 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-3-carboxamide (152 mg, 0.30 mmol), K3PO4.3H2O (200 mg, 0.76 mmol), Pd2(dba)3 (23 mg, 0.03 mmol) and X-Phos (23 mg, 0.06 mmol) in dioxane/H2O (2 mL/0.5 mL) was stirred at 110° C. for 1 hour. After the reaction, the mixture was filtered and the filtrate was diluted with water (20 mL) and extracted with EtOAc (20 mL*3). The organic layer was washed with brine (10 mL*3), dried over Na2SO4 and concentrated. The residue was purified by prep-HPLC to afford the product of 5-(6-(4-fluorobenzyl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (42 mg, yield: 27%). 1H-NMR (CDCl3, 400 MHz) δ 7.97˜8.02 (m, 3H), 7.82˜7.88 (m, 2H), 7.64 (s, 1H), 7.33˜7.36 (m, 2H), 7.22 (t, J=8.8 Hz, 2H) 7.18 (t, J=8.4 Hz, 2H), 6.08 (br s, 1H), 4.86 (s, 2H), 4.34 (s, 2H), 3.16 (s, 3H), 3.01 (d, J=4.8 Hz, 3H), 2.99 (s, 3H). MS (M+H)+: 617.

Provenance & Evidence