Allyltributylstannane → 8-Allyl-7-chloro-2-methoxy-[1,5]naphthyridine
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1OS(C(F)(F)F)(=O)=O)=[N:9][C:8]([O:20][CH3:21])=[CH:7][CH:6]=2.[CH2:22]([Sn](CCCC)(CCCC)CCCC)[CH:23]=[CH2:24]>CN(C=O)C>[CH2:24]([C:11]1[C:2]([Cl:1])=[CH:3][N:4]=[C:5]2[C:10]=1[N:9]=[C:8]([O:20][CH3:21])[CH:7]=[CH:6]2)[CH:23]=[CH2:22]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
A flask charged with trifluoromethanesulfonic acid 3-chloro-6-methoxy-[1,5]naphthyridin-4-yl ester (1.50 g; prepared according to WO 2004/058144), allyltributylstannane (1.68 g) and DMF was degassed with N2. The reaction mixture was treated with LiCl (695 mg) and Pd(PPh3)4 (126 mg) and further stirred at 100° C. for 4 h. After cooling, the mixture was poured into 10% aq. NH4OH and EA, the aq. layer was extracted with EA and the combined org. layers were washed with water (2×) and brine, dried over MgSO4 and concentrated. The residue was purified by CC (Hept/EA 4:1), affording a yellow oil (795 mg; 77% yield).
Aufarbeitung
- customwas degassed with N2
- additionThe reaction mixture was treated with LiCl (695 mg) and Pd(PPh3)4 (126 mg)
- temperatureAfter cooling
- additionthe mixture was poured into 10% aq. NH4OH and EA
- extractionthe aq. layer was extracted with EA
- washlayers were washed with water (2×) and brine
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe residue was purified by CC (Hept/EA 4:1)
- customaffording a yellow oil (795 mg; 77% yield)
Quellen und Nachweise
- ORD-Eintrag
- ord-218db01b57434a92bcc8829141098790
- Quelldatensatz
- uspto-grants-2013_06
- Patentnummer
- US08466168B2
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