[CH3:1][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].[C:10]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C(N=[CH:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1I)(C)(C)C.[CH3:48][N:49](C=O)C>[Pd].C(O)(=O)C>[CH3:10][C:43]1[CH:44]=[C:45]([C:1]2[N:49]=[CH:48][C:9]3[C:4]([C:2]=2[CH3:3])=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:46]=[C:41]([CH3:40])[CH:42]=1
Propane-2-yl-benzene (100 mmol), acetic acid palladium (2.7 mmol), triphenylphosphine (5 mmol), and sodium carbonate (50 mmol) were put in a dried two-neck round-bottom flask and dissolved in DMF (100 ml). Subsequently, tert-butyl-(2-iodo-benzylidene)amine (50 mmol) was added thereto. The resulting solution was stirred in a bath at 100° C. for 24 hours. After completion of the reaction, the temperature was allowed to cool to room temperature. The reaction mixture was extracted with ether and saturated NH4Cl. The extract was distilled under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane: EtOAc=5:1) to yield 3-(3,5-dimethylphenyl)-4-methylisoquinoline.
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