Potassium Carbonate → 4,5-Dibromo-1-ethyl-2-(naphthalen-1-yl)-1H-imidazole
Reaktionsgleichung
Br[C:2]1[N:3]([CH2:9][CH3:10])[C:4]([Br:8])=[C:5]([Br:7])[N:6]=1.[C:11]1(OB(C2C=CC=CC=2)O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:7][C:5]1[N:6]=[C:2]([C:19]2[C:20]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:16]=[CH:17][CH:18]=2)[N:3]([CH2:9][CH3:10])[C:4]=1[Br:8]Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
To a solution of 2,4,5-tribromo-1-ethyl-1H-imidazole (13.19 g, 40 mmol) and 1-naphthylphenylboronic acid (6.88 g, 40 mmol, 1.0 eq.) in toluene (100 ml) is added aqueous potassium carbonate solution (2.0 N, 40 ml, 2.0 eq.), followed by the addition of Pd(PPh3)4 (1.154 g, 1 mmol, 0.025 eq.). The resulting mixture is degassed with nitrogen, and then stirred at 90° C. for 16 hr. After cooling to rt, the reaction mixture is diluted with EtOAc (100 ml), washed with water and brine, and dried over sodium sulfate. After the solvent is removed, the crude product is purified through flash chromatography to afford the title product LCMS 380 (M+1).
Aufarbeitung
- customThe resulting mixture is degassed with nitrogen
- temperatureAfter cooling to rt
- additionthe reaction mixture is diluted with EtOAc (100 ml)
- washwashed with water and brine
- dry with materialdried over sodium sulfate
- customAfter the solvent is removed
- customthe crude product is purified through flash chromatography
Quellen und Nachweise
- ORD-Eintrag
- ord-707e734d43db4ad18a4482477ac34ea0
- Quelldatensatz
- uspto-grants-2010_06
- Patentnummer
- US07728009B1
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