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
Reaktionsgleichung
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[NH:4][C:3]=1/[CH:8]=[C:9]1\[C:10](=[O:25])[N:11]([C:18](N2C=CN=C2)=[O:19])[C:12]2[C:17]\1=[CH:16][CH:15]=[CH:14][CH:13]=2.[CH3:26][O:27][CH2:28][CH2:29][OH:30]>>[CH3:26][O:27][CH2:28][CH2:29][O:30][C:18]([N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)/[C:9](=[CH:8]/[C:3]2[NH:4][C:5]([CH3:7])=[CH:6][C:2]=2[CH3:1])/[C:10]1=[O:25])=[O:19]Komponenten
Versuchsvorschrift
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]+.)
Aufarbeitung
- custompartitioned between water and dichloromethane
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- concentrationconcentrated
- customThe residue was purified on a silica gel column
- washeluting with ethyl acetate-hexane (1:3)
Quellen und Nachweise
- ORD-Eintrag
- ord-57df25850ae84e0fb17b18b0bd1b2adb
- Quelldatensatz
- uspto-grants-2004_09
- Patentnummer
- US06797725B2
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