Reaktionsgleichung
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][C:9]#[C:10][CH3:11].[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+].C[N:21](C=O)C>C(OCC)(=O)C.[Cl-].[NH4+].C(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CO>[CH3:8][C:9]1[NH:21][C:7]2=[CH:2][N:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[CH3:11]Komponenten
Edukt 5
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 5
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
In a pressure tube, a solution of iodopyridine (1.80 g, 8.18 mmol) in 20 mL of DMF was treated with 2-butyne (1.5 mL, 19.1 mmol), Pd(dppf)2Cl2.CH2Cl2 (357 mg, 0.438 mmol), lithium chloride (367 mg, 8.71 mmol), and sodium carbonate (1.82 g, 17.2 mmol). The tube was sealed and heated to 90° C. After 24 hours, the tube was cooled and opened. The resulting mixture was diluted with 20 mL of ethyl acetate and 20 mL of saturated aqueous ammonium chloride solution. The phases were separated and the aqueous layer was extracted with three 50 mL portions of ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (CH2Cl2 to 10% MeOH in CH2Cl2, gradient) afforded the title product as a brown solid (920 mg, 77% yield).
Aufarbeitung
- customThe tube was sealed
- temperaturethe tube was cooled
- customThe phases were separated
- extractionthe aqueous layer was extracted with three 50 mL portions of ethyl acetate
- dry with materialThe combined organic layers were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-1b885b6059d946be93d874fc01006f08
- Quelldatensatz
- uspto-grants-2014_06
- Patentnummer
- US08741897B2
Verknüpfte Notizen
Wird geladen…