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

Participants

Reaction Steps

To a solution of (E)-tert-butyl 2-(3-(2-ethoxyvinyl)-6-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)pyridin-2-yl)-3-methyl-1H-indole-1-carboxylate (60 mg, 0.080 mmol) in 1,4-Dioxane (2 mL) was added 4 M HCl in dioxane (1 mL, 4.00 mmol). The resultant bright orange mixture was stirred at ambient temperature for 45 minutes then was heated at 60° C. for 1.75 h. The mixture was concentrated in vacuo, azeotroping from CH3CN, and the residue was diluted with saturated NaHCO3 (aq) solution and extracted into EtOAc. The organic layer was washed with brine (1×), dried over MgSO4, concentrated in vacuo, and purified by silica gel column chromatography using a gradient of 0-70% EtOAc/Hexanes as eluent. Lyophilization from CH3CN/H2O provided the title compound. 1H NMR δ (ppm) (CHCl3-d): 8.27 (1H, s), 8.14 (1H, d, J=7.34 Hz), 8.09˜8.05 (2H, m), 7.91˜7.84 (3H, m), 7.71˜7.68 (2H, m), 7.46˜7.43 (2H, m), 7.24 (2H, t, J=8.65 Hz), 6.61 (1H, d, J=7.33 Hz), 5.96 (1H, br s), 3.35 (3H, s), 3.06 (6H, m), 2.73 (3H, s). MS (M+H): 607.

Provenance & Evidence