Reaktionsgleichung
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:17]([O:19][C:20](=[O:29])[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23](Br)[CH:22]=1)[CH3:18]>[Cu]I>[CH2:17]([O:19][C:20](=[O:29])[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([N:7]2[C:8]([NH2:10])=[CH:9][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:6]2)[CH:22]=1)[CH3:18]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
3-(Tert-butyl)-1H-pyrazol-5-amine (1.10 g, 7.90 mmol), potassium carbonate (2.29 g, 16.6 mmol), and copper (I) iodide (75.0 mg, 1.58 mmol) were weighed into a microwave vial and purged with argon. 3-Bromo-5-chloro-benzoic acid ethyl ester (2.50 g, 9.49 mmol) was then added, followed by trans-N,N′-dimethylcyclohexane-diamine (225 mg, 1.58 mmol) and the reaction vessel purged with argon. The reagents were then solvated with toluene (8 mL), and then degassed with argon, sealed and subjected to microwave irradiation (135° C., 6 h). The reaction mixture was filtered through Celite, concentrated in vacuo and purified by FCC, eluting with 0-10% EtOAc/cyclohexane, to afford the title compound (489 mg, 19%). LCMS (Method 3) Rt 4.26 min, 322.1 [MH+].
Aufarbeitung
- custompurged with argon
- customthe reaction vessel purged with argon
- customdegassed with argon
- customsealed
- customsubjected to microwave irradiation (135° C., 6 h)
- filtrationThe reaction mixture was filtered through Celite
- concentrationconcentrated in vacuo
- custompurified by FCC
- washeluting with 0-10% EtOAc/cyclohexane
Quellen und Nachweise
- ORD-Eintrag
- ord-7f6e2e9652804116b1b191dc45c8235d
- Quelldatensatz
- uspto-grants-2016_09
- Patentnummer
- US09440974B2
Verknüpfte Notizen
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