[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl[C:48]1[CH:55]=[C:54]([NH2:56])[CH:53]=[CH:52][C:49]=1[C:50]#[N:51]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[NH2:56][C:54]1[CH:55]=[C:48]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:49]([C:50]#[N:51])=[CH:52][CH:53]=1534 mg of phenylboronic acid, 79 mg of palladium(II) acetate, 287 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, 1.486 g of potassium phosphate (K3PO4) and 305 mg of 2-chloro-4-aminobenzonitrile were suspended in 7 ml of toluene and stirred at 80° C. under an argon atmosphere for 12 h. The cooled reaction mixture was admixed with water and ethyl acetate and filtered. The filtrate was extracted three times with a mixture of ethyl acetate and toluene. The organic phases were removed, dried over magnesium sulfate, filtered and concentrated under reduced pressure. 1H NMR: 7.52-7.42, m, 6H, 6.63, m, 2H, 6.25, s (broad), 2H.
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