3- Pyridylmagnesium chloride

Some heteroaryl halides are electron-deficient and reactive. 3-Pyridylmagnesium chloride (13) was prepared efficiently by the treatment of 3-bromopyridine (12) with isopropylmagnesium chloride, and 2-(3-pyridyl)pyridine (15) was prepared by coupling 13 with 2-bromopyridine (14) using DPPF as a ligand [71]. 

Cross-coupling reactions of 3-pyridylmagnesium chlorides with haloazines or halodiazines in the presence of a catalytic amount of Ni(acac)2 and dppe at room temperature afford the corresponding 3-pyridylazines in good yields [33]. 

---