Preparation of 2-substituted pyridines

Details Preparation of 2-substituted pyridines Preparation of 2-substituted pyridines

1999-05-05

2000-04-25

Morris, Patricia L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546 4, 546294, 546296, 546298, 546301, 546302, 546303, 546314, 546348, C07F 722, C07F 710, C07D21371, C07D21370

Patent

active

060545836

ABSTRACT:
This invention relates to a process for preparing 2-substituted pyridines via metal halogen exchange with sec-butyllithium on optionally substituted 2-bromo or 2-iodopyridines. The resulting lithopyridine intermediate is reacted with an electrophile to provide the desired 2-substituted pyridine. The substitution of sec-butyllithium for n-butyllithium in such a process results in an enhanced yield and purity of the desired 2-substituted pyridine.

REFERENCES:
Dongwei, C., et al., "A Study of the Lithiation of 2,6-Dibromopyridine with Butyllithium, and its Application to Synthesis of L-739,010", Tetrahedron Letters, vol. 37, No. 15, pp. 2537-2540 (Apr. 8, 1996).
Gilman, H., et al., "Some 2-Pyridlmetallic Compounds", Journal of Organic Chemistry, vol. 16, pp. 1788-1791 (1951).

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