Br[C:2]1[C:7]([N:8]([CH3:10])[CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)#[CH:12].C(N(CC)CC)C.[Cl-].[NH4+]>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)I.CN(C)C=O>[CH3:9][N:8]([CH3:10])[C:7]1[C:2]([C:12]#[C:11][C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:3][CH:4]=[CH:5][CH:6]=1A mixture of 2 g of (2-Bromo-pyridin-3-yl)-dimethyl-amine (9.95 mmoles), 1.24 g of 4-ethynyl pyridine (12 mmoles) in 120 mL of a 1/1 mixture of triethylamine and dimethylformamide is stirred under argon at room temperature. 750 mg of bis(triphenylphosphine)palladium dichloride and 400 mg of copper iodide are added to the reaction mixture which is further stirred at room temperature for 3 hours. The reaction mixture is poured into ammonium chloride solution and extracted with ethyl acetate. The organic phase is washed with water and dried over magnesium sulfate. The solid residue after concentration is purified by chromatography on silica gel (ethylacetate/hexane 1/1) to give 1 g of Dimethyl-(2-pyridin-4-ylethynyl-pyridin-3-yl)-amine as orange oil.
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