Preparation of 5-brominated and 5,5'-dibrominated 2,2'-bipyridines and 2,2'-bipyrimidines.

doi:10.1021/JO010707J

Paper

Preparation of 5-brominated and 5,5'-dibrominated 2,2'-bipyridines and 2,2'-bipyrimidines.

Published Jan 3, 2002 · P. Schwab, F. Fleischer, J. Michl

The Journal of organic chemistry

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131

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Abstract

Efficient syntheses of 5-brominated and 5,5'-dibrominated 2,2'-bipyridines and 2,2'-bipyrimidines, useful for the preparation of metal-complexing molecular rods, have been developed. 5-Bromo-2,2'-bipyridine, 5-bromo-5'-n-butyl-2,2'-bipyridine, and 5-bromo-5'-n-hexyl-2,2'-bipyridine were obtained by Stille coupling of 2,5-dibromopyridine with 2-trimethylstannylpyridine or the requisite 5-alkyl-2-trimethylstannylpyridine, obtained via regioselective zincation of a 3-alkylpyridine.BF(3) complex in the less hindered of the two reactive positions with lithium di-tert-butyl-(2,2,6,6-tetramethylpiperidino)zincate. 5,5'-Dibromo-2,2'-bipyridine was obtained by the reductive symmetric coupling of 2,5-dibromopyridine with hexa-n-butyldistannane. The yields of these coupling reactions ranged from 70 to 90%. 5-Bromo- and 5,5'-dibromo-2,2'-bipyrimidines were obtained in yields of 30 and 15%, respectively, by bromination of 2,2'-bipyrimidine, prepared from 2-chloropyrimidine in 80% yield by an improved reductive symmetric coupling procedure.

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Efficient syntheses of 5-brominated and 5,5'-dibrominated 2,2'-bipyridines and 2,2'-bipyrimidines enable the preparation of metal-complexing molecular rods with high yields.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Preparation of 5-brominated and 5,5'-dibrominated 2,2'-bipyridines and 2,2'-bipyrimidines.

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References

Citations

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