Potassium Carbonate → 4-(2-methoxy-4-nitrophenyl)-1-methyl-1H-pyrazole
Reaktionsgleichung
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[CH3:13][N:14]1[CH:18]=[C:17](B2OC(C)(C)C(C)(C)O2)[CH:16]=[N:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[C:17]1[CH:16]=[N:15][N:14]([CH3:13])[CH:18]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 150 °C
Versuchsvorschrift
Step K (1): [1,1′-Bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (1:1 complex with dichloromethane, 7.0 g, 8.62 mmol) was added to a degassed mixture of 1-bromo-2-methoxy-4-nitrobenzene (20 g, 86.2 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (23.3 g, 112 mmol), and potassium carbonate (23.6 g, 122 mmol) in DMF (200 mL). The mixture was heated at 150° C. for 18 h. The crude reaction mixture was cooled to rt and filtered through diatomaceous earth (Celite®). The reaction mixture was diluted with EtOAc (200 mL) and washed with water and then brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography (EtOAc/hexane) to afford 4-(2-methoxy-4-nitrophenyl)-1-methyl-1H-pyrazole (14 g, 70% yield).
Aufarbeitung
- customThe crude reaction mixture
- temperaturewas cooled to rt
- filtrationfiltered through diatomaceous earth (Celite®)
- additionThe reaction mixture was diluted with EtOAc (200 mL)
- washwashed with water
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified
Quellen und Nachweise
- ORD-Eintrag
- ord-adb0826affb44dbe8dadcc885db26074
- Quelldatensatz
- uspto-grants-2013_01
- Patentnummer
- US08349880B2
Notizen zur Reaktion
Wird geladen…