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Unexpected product distributions in the synthesis of 2,6-bis-(indazolyl)pyridine and 2-(pyrazol-1-yl)-6-(indazolyl)pyridine

✍ Scribed by Ruth Pritchard; Colin A. Kilner; Malcolm A. Halcrow

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
260 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

a b s t r a c t Reaction of 2-bromopyridine with 2 equiv of sodium indazolide in diglyme at 140 Β°C affords 2,6-bis-(indazol-1-yl)pyridine and 2-(indazol-1-yl)-6-(indazol-2-yl)pyridine in purified yields of 24% and 68% respectively. A similar reaction, using 1 equiv of sodium indazolide at 70 Β°C, gives a low-yield mixture of 2-(indazol-1-yl)-6-bromopyridine and 2-(indazol-2-yl)-6-bromopyridine. Both these intermediates are transformed into 2-(pyrazol-1-yl)-6-(indazol-1-yl)pyridine and 2,6-di(pyrazol-1-yl)pyridine upon treatment with 1 equiv of sodium pyrazolide in diglyme at 140 Β°C. These observations imply that the indazolyl group is a leaving group comparable to a bromo substituent under nucleophilic attack by pyrazolide or indazolide ions under these conditions. No reaction was observed between 2-(pyrazol-1yl)-6-bromopyridine and 1 equiv of sodium indazolide under the same conditions. A single crystal structure of its iron(II) complex confirmed the regiochemistry of 2,6-bis-(indazol-1-yl)pyridine, and revealed significant conformational flexibility in the distal ligand indazolyl groups.

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