Nitrogen → HCID 131729997, compound

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 2-bromo-4-(tert-butyl-dimethyl-silanyloxymethyl)-pyridine (1.04 g, 3.44 mmol) in dry Et2O (50 mL) was added n-BuLi (1.60 mL of a 2.5M solution in hexanes, 3.96 mmol) at −78° C. The reaction mixture was then stirred for 1 h at −78° C. before N,N-dimethylacetamide (0.64 mL, 6.88 mmol) was added dropwise. The reaction mixture was allowed to warm up to rt and stirred at this temperature for 10 min. Sat. aq. NH4Cl (20 mL) was added, the layers separated and the aq. layer extracted with Et2O (3×30 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:1 to 5:1 hept-EA) gave the title compound as a pale yellow oil. TLC: rf (1:2 hept-EA)=0.64. LC-MS-conditions 02: tR=1.12 min; [M+H]+=265.84.

Provenance & Evidence