Stannane → Methyl 2-[6-(methyloxy)-1,5-naphthyridin-4-yl]-2-propenoate

HRID 15295

Reaktionsgleichung

[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2OS(C(F)(F)F)(=O)=O.C([Sn](CCCC)(CCCC)[C:26](=[CH2:31])[C:27]([O:29][CH3:30])=[O:28])CCC.[SnH4].[Li+].[Cl-]>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.[Cu]I>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[C:26](=[CH2:31])[C:27]([O:29][CH3:30])=[O:28]

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

To a solution of 1,1,1-Trifluoro-methanesulfonic acid 6-methoxy-[1,5]naphthyridin-4-yl ester (for a synthesis see WO2003010138, Example 1(b))(5.936 g, 15.83 mmol) in DMF (10 ml) was added methyl 2-(tributylstannanyl)-2-propenoate (for a synthesis of this stannane see Zhang, H. X.; Guibe, F.; Balavoine, G. J. Org. Chem. (1990), 55(6), 1857.) (7.312 g, 23.74 mmol), Pd(PPh3)4 (1.83 g, 1.58 mmol), CuI (2.26 g, 11.87 mmol) and LiCl (673 mg, 15.83 mmol). The reaction was stirred for 1 h at 25° C. after which time the solvent was evaporated. The residue was chromatographed on silica eluting with a gradient of 10% ethyl acetate in hexane affording the desired compound as a brown solid (3.603 g, 93%).

Aufarbeitung

customwas evaporated
customThe residue was chromatographed on silica eluting with a gradient of 10% ethyl acetate in hexane affording the desired compound as a brown solid (3.603 g, 93%)

Quellen und Nachweise

ORD-Eintrag: ord-58b802f4f8dc4005b21bfc0fff3d3a93
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07732461B2

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