A synthesis of methyl 3-(2-methoxy-4-pyridy1)propionate ( Z ) , a key intermediate in the synthesis of the potent long-acting histamine H,-receptor antagonist SK&F 93574 ( I ) , is described. The key step in the synthesis of compound (1 ) involves alkylation of 2-methoxy-4-methylpyridine (5) with sodium chloroacetate in the presence of sodamide. The scope and limitations of the alkylation is investigated using a variety of electrophiles. The application of this reaction to other 2-substituted 4-methylpyridines is also discussed.
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