7- Azaindole 4-chloro-, nucleophilic substitution

Only a few examples of nucleophilic substitution have been reported - displacement of halogen a and y to the pyridine nitrogen can be carried out under vigorous conditions or with long reaction times. No Chichibabin substitutions have been reported. Reaction of 4-chloro-7-azaindole with a secondary amine results in normal substitution of the halogen, but reaction with primary amines gives 5-azaindole rearrangement products by the sequence shown below. ... 

The reactivity of 4-chloro-l-methyl-5-azaindole, for which data is available, towards nucleophilic substitution of chlorine by piperidine can be usefully compared with that of some related systems it is significantly less reactive than the most closely related bicyclic systems, probably due to increased electron density in the six-membered ring resulting from donation from N-1. 

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See also in sourсe #XX -- [ ]

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