Reaktionsgleichung
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N:9]=[C:10]=[O:11].NC1C=CC([C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[NH:21][C:20]=2[C:28]([NH2:30])=[O:29])=CC=1>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:11])[NH:9][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:26]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:27]=1[CH:19]=[C:20]([C:28]([NH2:30])=[O:29])[NH:21]2Komponenten
Reaktionsbedingungen
- Temperatur
- 20 °C
Versuchsvorschrift
0.115 cm3 (0.876 mmol) of 2-fluoro-5-methylphenyl isocyanate is added, at a temperature in the region of 20° C., under an argon atmosphere, to 0.2 g (0.796 mmol) of 3-(4-aminophenyl)-1H-indole-2-carboxamide in solution in 10 cm3 of tetrahydrofuran. After stirring for 18 hours at a temperature in the region of 20° C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa), to give 400 mg of a residue which is purified by flash chromatography [eluent: ethyl acetate/cyclohexane (7/3 by volume)]. After concentration under reduced pressure of the fractions containing the expected product, 250 mg of a yellow residue are obtained, which residue is stirred in 10 cm3 of dichloromethane and then filtered and dried under reduced pressure (2.7 kPa), to give 180 mg of 3-{4-[3-(2-fluoro-5-methylphenyl)ureido]phenyl}-1H-indole-2-carboxamide, in the form of a beige solid that melts at 220° C.;
Aufarbeitung
- concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
Quellen und Nachweise
- ORD-Eintrag
- ord-bacf64b2350944daa124f842c48100cb
- Quelldatensatz
- uspto-grants-2009_07
- Patentnummer
- US07566736B2
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