Nitrogen → 2-Acetyl-6-bromopyridine
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N#N.Br[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[N:5]=1.[Li]CCCC.[NH4+].[Cl-].[CH3:18][CH2:19][O:20]CC>CCCCCC>[Br:10][C:6]1[N:5]=[C:4]([C:19](=[O:20])[CH3:18])[CH:9]=[CH:8][CH:7]=1N#N.Br[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[N:5]=1.[Li]CCCC.[NH4+].[Cl-].[CH3:18][CH2:19][O:20]CC>CCCCCC>[Br:10][C:6]1[N:5]=[C:4]([C:19](=[O:20])[CH3:18])[CH:9]=[CH:8][CH:7]=1In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a suspension of 2,6-dibromopyridine (2.44 g, 10.00 mmol) in ether (25.0 mL) was treated at −78° C. with n-BuLi (4.0 mL of a 2.5M solution in hexane, 10.00 mmol). The reaction mixture was stirred for 30 min before N,N-dimethylacetaminde (1.50 mL, 16.13 mmol) was added and the solution was then allowed to warm to rt over 1 h. Sat. aq. NH4Cl was then added and the aq. layer was extracted with Et2O (2×50 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (20:1 hept-EA) gave the title compound as a white solid: TLC:rf (20:1 hept-EA)=0.25. LC-MS-conditions 02: tR=0.98 min.
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