Triphenylphosphine → 2-(4-fluorophenyl)-N-methyl-5-(12-methyl-5,6-dihydroindolo[1,2-h][1,7]naphthyridin-2-yl)-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

Participants

Reaction Steps

To a mixture of 2-(4-fluorophenyl)-5-(5-(2-hydroxyethyl)-6-(3-methyl-1H-indol-2-yl)pyridin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (43 mg, 0.069 mmol) and triphenylphosphine (90 mg, 0.343 mmol) in THF (4 mL) was diisopropyl azodicarboxylate (0.067 mL, 0.343 mmol). The resultant mixture was stirred at ambient temperature for 16 h, diluted with EtOAc and washed successively with H2O (2×) and brine (1×). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography using a step gradient of 0-40-90% EtOAc/Hexanes as eluent. Further purification by silica gel column chromatography with a gradient of 0-10% EtOAc/CH2Cl2 as eluent, followed by lyophilization from CH3CN/H2O provided the title compound. 1H NMR δ (ppm) (CHCl3-d): 8.16 (1H, s), 8.07˜8.03 (2H, m), 7.70˜7.66 (3H, m), 7.47 (1H, d, J=7.77 Hz), 7.37 (1H, d, J=8.24 Hz), 7.32 (1H, D, J=7.1 Hz), 7.26˜7.22 (2H, m), 7.16 (1H, t, J=7.40 Hz), 5.95 (1H, br s), 4.34 (2H, t, J=6.37 Hz), 3.32 (3H, s), 3.28 (2H, t, J=6.4 Hz), 3.05 (3H, d, J=4.91 Hz), 2.83 (3H, s), 2.75 (3H, s). MS (M+H): 609.

Provenance & Evidence