Cl[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].C[O-].C([Sn+](CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C([O:38][C:39]([CH3:41])=[CH2:40])(=O)C>C(OCC)C.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.Cl[Pd]Cl>[CH3:8][O:7][C:5](=[O:6])[C:4]1[CH:3]=[C:2]([CH2:40][C:39](=[O:38])[CH3:41])[N:11]=[C:10]([Cl:12])[CH:9]=1Add methyl 2,6-dichloroisonicotinate (3.0 g, 15.0 mmol), trans-dichlorobis(tri-o-tolylphosphine)palladium (II) (196 mg, 0.25 mmol), tributyltin methoxide (2.4 g, 7.5 mmol) and toluene (20 mL) in a previously nitrogen filled sealed vessel. Flush the reactants with nitrogen again. Add isopropenyl acetate (0.85 mL, 7.75 mmol) under nitrogen and heat the sealed mixture at 100° C. overnight with vigorous stirring. Cool the reaction to room temperature, dilute with diethyl ether and filter through a filtering agent. Concentrate and purify (silica gel chromatography, eluting with 0:100 to 20:80 ethyl acetate:hexanes) to give the title compound (29%).
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