Can be metallated at the 3-position with LDA at -70o: J. Org. Chem., 53, 1367 (1988). With the unimetal superbase complex formed from 2 mol of n-BuLi and I mol of 2-(Dimethyl-amino)-ethanol, in hexane, products are obtained resulting from apparent metallation at the 6-position. A radical mechanism, rather than a true 6-metallation, has been proposed for this reaction: J. Chem. Soc., Perkin 1, 3071 (1997). Analogous results have been reported with 2-chloropyridine: Org. Lett., 2, 803 (2000).
