[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](Cl)[N:7]=[C:6]([Cl:11])[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C@@H:65]([NH2:69])([CH2:67][CH3:68])[CH3:66]>C1(C)C=CC=CC=1.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:5]=[C:6]([Cl:11])[N:7]=[C:8]([NH:69][C@H:65]([CH2:67][CH3:68])[CH3:66])[CH:9]=1Dissolve 2,6-dichloro-isonicotinic methyl ester (2.0 g, 10 mmol), palladium (II) acetate (224.0 mg, 1.0 mmol), racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (632 mg, 1.0 mmol) and cesium carbonate (3.96 g, 12 mmol) in toluene (20 mL) in a previously degassed sealed vessel. Flush the mixture with nitrogen gas. Add (S)-(+)-sec-butylamine (1.2 mL, 12 mmol) to the solution and heat the sealed mixture overnight at 100° C. Cool to room temperature and dilute with diethyl ether and filter through a filtering agent. Concentrate the filtrate and purify (silica gel chromatography, eluting with 0:100 to 10:90 ethyl acetate:hexanes) to give the title compound (73%).
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