Reductive Amination of Ethynylpyridines with Sodium Cyanoborohydride

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In order to investigate the structure-activity relationship of betahistine derivatives, a general synthesis of methylated 2-(2-methylaminoethyl) pyridines was developed based on the addition of methylamine hydrochloride to methylated 2-ethynylpyridines under reductive conditions. In addition, the scope and limitations of the reductive addition were briefly examined. For example, the reaction proceeded smoothly with p-nitrophenylacetylene, whereas phenylacetylene itself did not react with methylamine.

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