[C:1]([C:3]1[CH:4]=[C:5]([CH3:18])[C:6]([NH:9][C:10](=[O:17])[CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[N:7][CH:8]=1)#[CH:2].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[CH:28][C:29](I)=[N:30][CH:31]=2)=[CH:22][CH:21]=1.N1CCCCC1>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]2[CH:27]=[CH:28][C:29]([C:2]#[C:1][C:3]3[CH:4]=[C:5]([CH3:18])[C:6]([NH:9][C:10](=[O:17])[CH2:11][N:12]4[CH2:16][CH2:15][CH2:14][CH2:13]4)=[N:7][CH:8]=3)=[N:30][CH:31]=2)=[CH:24][CH:25]=1Under an argon atmosphere 4 mg (0.01 mmol) Pd(PPh3)2Cl2 and 1 mg (0.01 mmol) CuI are added to a solution of 73 mg (0.3 mmol) N-(5-ethynyl-3-methyl-pyridin-2-yl)-2-pyrrolidin-1-yl-acetamide and 95 mg (0.3 mmol) 5-(4-chloro-phenyl)-2-iodo-pyridine in 59 μL (0.6 mmol) piperidine and 10 mL THF and the reaction mixture is stirred for 30 min at RT. It is evaporated down i.vac., the residue is taken up in EtOAc, the organic phase is washed with water and saturated NaCl solution and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified first by chromatography (silica gel, EtOAc/MeOH/NH3 95:5:0.5) and then by HPLC.
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