Reaktionsgleichung
[N:1]1([C:6]2[CH:27]=[CH:26][C:9]([CH2:10][C:11]3[C:12](OC)=NC4C([C:20]=3[Cl:21])=CC(Br)=CC=4C)=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[Br:28][C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[C:31]([F:36])[CH:30]=1.O=P(Cl)(Cl)[Cl:39]>>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH2:10][C:11]3[C:20]([Cl:21])=[N:33][C:32]4[C:34]([C:12]=3[Cl:39])=[CH:35][C:29]([Br:28])=[CH:30][C:31]=4[F:36])=[CH:26][CH:27]=2)[CH:5]=[CH:4][CH:3]=[N:2]1Komponenten
4
Reaktionsbedingungen
- Temperatur
- 105 °C
Versuchsvorschrift
A mixture of 2-(4-(1H-pyrazol-1-yl)benzyl)malonic acid (4 g, 15.37 mmol, Intermediate 6: step b) and 4-bromo-2-fluoroaniline (2.7 g, 13.973 mmol) in POCl3 (20 mL) was heated at 105° C. for 3 hours, cooled to room temperature and evaporated in vacuo to remove excess POCl3. The residue was poured into ice H2O and treated with aqueous NH4OH to pH 8-9 (temperature of the aqueous mixture was kept cold during addition). The precipitates were collected, rinsed with H2O and dried under reduced pressure. The solids were diluted with DCM and insoluble solids filtered off. The filtrate was evaporated to dryness to provide product as a tan solid.
Aufarbeitung
- temperaturecooled to room temperature
- customevaporated in vacuo
- customto remove excess POCl3
- additionThe residue was poured into ice H2O
- additiontreated with aqueous NH4OH to pH 8-9 (temperature of the aqueous mixture
- additionwas kept cold during addition)
- customThe precipitates were collected
- washrinsed with H2O
- customdried under reduced pressure
- additionThe solids were diluted with DCM and insoluble solids
- filtrationfiltered off
- customThe filtrate was evaporated to dryness
- customto provide product as a tan solid
Quellen und Nachweise
- ORD-Eintrag
- ord-c2f704ef51e84d1c978674d2b298a349
- Quelldatensatz
- uspto-grants-2016_03
- Patentnummer
- US09290476B2
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