Regioselective halogenation of nicotine and substituted...

Details Regioselective halogenation of nicotine and substituted... Regioselective halogenation of nicotine and substituted...

2007-02-20

2007-02-20

Morris, Patricia L. (Department: 1625)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

11413281

ABSTRACT:
A first aspect of the present invention is a method for of making a compound of Formula Ia or Formula Ib:wherein X is halo, by (a) metalating a precursor compound to form an organometallic intermediate, and then reacting the organometallic intermediate with a halogenating agent to produce the compound of Formula Ia or Formula Ib.

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Gros et al. Lithiation of 2-Heterosubstituted Pyridines with BuLi-LiDMAE: Evidence for Regiospecificity at C-6.Journal of Organic Chemistry,67, 234-237, 2002.
Kondo et al. TMP-Zincate as Highly Chemoselective base for Directed Ortho Metalation.Journal of the American Chemical Society,121, 3539-3540, 1999.
Bleicher, et al. A Practical and Efficient Synthesis of the Selective Neuronal Acetylcholine-Gated Ion Channel Agonist (S)-(-)-5-Ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine Maleate (SIB-1508Y).J. Org. Chem.63: 1009-1118 (1998).
Brown, et al. A Convenient Synthesis of Dimethyl (Diazomethyl)phosphate (Seyferth/Gilbert Reagent).J. Org. Chem.61:2540-2541 (1996).

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