Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH2:8]([OH:12])[CH2:9][C:10]#[CH:11].C(N(CC)CC)C.O>C(Cl)Cl.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.C(OCC)(=O)C>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:11]#[C:10][CH2:9][CH2:8][OH:12])[CH:3]=1
To a stirred solution of 3-bromopyridine (3.75 g, 23.8 mmol), 3-butyn-1-ol (2.0 g, 28.5 mmol) and triethylamine (12 ml) in anhydrous DCM was added bis(triphenylphosphine)palladium dichloride (0.05 g, 0.07 mmol) and copper(I) iodide (0.05 g, 0.26 mmol). The mixture was refluxed for 20 h under argon. After cooling, water (20 ml) was added and the product extracted into DCM. The combined organics were dried over anhydrous potassium carbonate, filtered and evaporated to give a brown oil. Column chromatography (flash silica gel, ethyl acetate) gave 4-(3-pyridyl)-1-but-3-ynol (0.43 g, 12%) as a colourless oil.
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