Tributylvinyltin → 6-Ethenyl-3,4-dihydro-1,8-naphthyridin-2(1H)-one
Reaktionsgleichung
Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[CH2:13]([Sn](CCCC)(CCCC)C=C)[CH2:14]CC>CN(C=O)C.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>[CH:13]([C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2)=[CH2:14]Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 105 °C
Versuchsvorschrift
6-Bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one (113e) (4.6 g, 20.3 mmole) and tributyl(vinyl)tin (7.7 g, 24.4 mmole) were dissolved in DMF (200 mL) and the solution was degassed with nitrogen. (Ph3P)4Pd (590 mg, 0.5 mmole) was added to the solution. The reaction was heated to 105° C. under nitrogen overnight, then was cooled to room temperature and filtered through a sintered glass funnel. The filtrate was washed with NH4OH and extracted with EtOAc (2×150 mL). The combined organic phases were washed with brine, dried over Na2SO4 and concentrated in vacuo to afford the title compound (2.1 g, 60%) as an off white solid: MS (ES) m/e 175 (M+H)+.
Aufarbeitung
- customthe solution was degassed with nitrogen
- temperaturewas cooled to room temperature
- filtrationfiltered through a sintered glass funnel
- washThe filtrate was washed with NH4OH
- extractionextracted with EtOAc (2×150 mL)
- washThe combined organic phases were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-c0d8523c87354d54ba36574e0cccb338
- Quelldatensatz
- uspto-grants-2007_04
- Patentnummer
- US07205408B2
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