2-Methoxyethanol → 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 2-methoxy-ethyl ester

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Reaktionsschritte

A reaction mixture of 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-1-(imidazol-1-ylcarbonyl)-1,3-dihydro-indol-2-one (200 mg, 0.6 mmol) in 6 mL of 2-methoxyethanol was stirred at room temperature for 20 h and partitioned between water and dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified on a silica gel column eluting with ethyl acetate-hexane (1:3) to give 3-[1-(3,5-dimethyl-1H-pyrrol-2-yl)-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid 2-methoxy-ethyl ester (63 mg, 31%) as an red solid. 1H NMR (400 MHz, CDCl3) δ 12.71 (s, 1H, NH-1′), 7.85 (d, J=7.05 Hz, 1H), 7.50 (d, J=7.05 Hz, 1H), 7.40 (s, 1H, H-vinyl), 7.16–7.23 (m, 2H), 6.03 (s, br, 1H, H-4′), 4.62 (t, J=4.70 Hz, 2H, CH2), 3.81 (t, J=4.70 Hz, 2H, CH2), 2.38 (s, 3H, CH3), and 2.34 (s, 3H, CH3). MS m/z (relative intensity, %) 341 (100, [M+1]+.).

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