Reaktionsgleichung
[C:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[F:10])[NH2:6])#[N:2].[N:11]([O-])=O.[Na+].C(O)(=O)C.[Br:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][C:29]([C:32](=O)[CH3:33])=[C:28](O)[C:27]2=[O:36])=[CH:22][CH:21]=1>Cl.O.CO>[C:1]([C:3]1[CH:4]=[C:5]([N:6]2[C:28]3[C:27](=[O:36])[N:26]([C:23]4[CH:24]=[CH:25][C:20]([Br:19])=[CH:21][CH:22]=4)[CH2:31][CH2:30][C:29]=3[C:32]([CH3:33])=[N:11]2)[CH:7]=[CH:8][C:9]=1[F:10])#[N:2]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
3-Cyano-4-fluoroaniline (3.7 mmol, 0.5 g) in conc. HCl (4 mL) was cooled to 0° C. and NaNO2 (4.4 mmol, 0.3 g) in water (3 mL). This was stirred at 0° C. for 30 min, then acetic acid (1.3 mL) was added. SnCl2·(H2O)2 (8.5 mmol, 1.9 g) in 1:1 water:conc. HCl (3 mL) was added dropwise to the cold solution and stirred for an additional 30 min. To this mixture 1-[4-bromophenyl]-3-hydroxy-4-acetyl-5,6-dihydropyridin-2-one (3.9 mmol, 1.2 g) was slurried in MeOH (20 mL) and added with the aid of additional MeOH (6 mL). The suspension was heated at 50° C. for 3 h, then cooled at 10° C. for 18 h. The product, 1-[3-cyano-4-fluorophenyl]-3-methyl-6-[4-bromophenyl]-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one, was isolated by filtration. There was obtained 1.34 g (3.2 mmol) of product; mp 237.6° C., LRMS (M+H)+: 425.2/427.1 m/z.
Aufarbeitung
- stirringstirred for an additional 30 min
- temperatureThe suspension was heated at 50° C. for 3 h
- temperaturecooled at 10° C. for 18 h
Quellen und Nachweise
- ORD-Eintrag
- ord-12a5c411a99d44ab854390aad4e69c82
- Quelldatensatz
- uspto-grants-2005_02
- Patentnummer
- US06858616B2
Verknüpfte Notizen
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