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Under a nitrogen atmosphere, zinc dust (4.06 g, 62.1 mmol) was suspended in N,N-dimethylacetamide (5 mL) and a mixture of trimethylsilylchloride (0.946 mL, 7.30 mmol) and 1,2-dibromoethane (0.636 mL, 7.30 mmol) was added cautiously over 10 min. After stirring for a further 15 min, a solution of N-(tert-butoxycarbonyl)-4-iodopiperidine (16.74 g, 51.11 mmol) in N,N-dimethylacetamide (20 mL) was added over 30 min and stirring was continued for an additional 30 min. In the open atmosphere, this mixture was filtered through Celite as quickly as possible, rinsing with a small amount of N,N-dimethylacetamide. The resulting yellow solution was injected into a separately prepared, nitrogen flushed suspension of [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.35 g, 1.83 mmol), copper(I) iodide (695 mg, 3.65 mmol) and 2,6-dichloro-4-iodopyridine (10.0 g, 36.5 mmol) in N,N-dimethylacetamide (30 mL) and this mixture was stirred at 80° C. for 16.5 hr. After cooling to rt, the mixture was diluted with EtOAc and water and partitioned. Filtration through Celite was necessary to break the emulsion, following which, the organics were washed with water and then dried over MgSO4. After being freed of volatiles, the resultant residue was purified by flash column chromatography (100:0-70:30 heptanes/EtOAc) to afford tert-butyl 4-(2,6-dichloro-4-pyridyl)piperidine-1-carboxylate as a white solid (7.49 g, 62%); 1H NMR (400 MHz, CDCl3) δ 7.11 (s, 2H), 4.19 (m, 2H), 2.78 (m, 2H), 2.71 (m, 1H), 1.81 (m, 2H), 1.65 (m, 2H), 1.48 (s, 9H).

1. additionwas added cautiously over 10 min
2. stirringstirring
3. waitwas continued for an additional 30 min
4. filtrationIn the open atmosphere, this mixture was filtered through Celite as quickly as possible,
5. washrinsing with a small amount of N,N-dimethylacetamide
6. customa separately prepared
7. customnitrogen flushed
8. stirringthis mixture was stirred at 80° C. for 16.5 hr
9. custompartitioned
10. filtrationFiltration through Celite
11. washthe organics were washed with water
12. dry with materialdried over MgSO4
13. customthe resultant residue was purified by flash column chromatography (100:0-70:30 heptanes/EtOAc)