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The best result we were able to obtain was the formation of 5-methyl-5′-[(trimethylsilyl)ethynyl]-2,2′-bipyridine (19) in 45% yield after lithiation of our model substrate 2-chloro-5-methyl-pyridine (9) with 2 equiv. of lithium and 4 equiv. of naphthalene, transmetallation with anhydrous zinc(II) chloride and subsequent palladium-catalysed cross-coupling reaction with 2-chloro-5-[(trimethylsilyl)ethynyl]-pyridine (8). However, the very long reaction time, which was found to be essential, residual unreacted lithium, which possibly interferes in the cross-coupling step, and also the excess of naphthalene caused problems during the isolation and purification of the product.
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