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

Participants

Reaction Conditions

Reaction Steps

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%).

Provenance & Evidence