Nitrogen → HCID 86650888, 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 3-bromo-5-(2-methyl-[1,3]dioxolan-2-yl)-pyridine (450 mg, 1.84 mmol) in Et2O (40.0 mL) at −78° C. was added dropwise n-BuLi (0.72 mL of a 2.5M solution in hexane, 1.88 mmol). The reaction mixture was then stirred at −78° C. for 30 min before DMF (0.17 mL, 2.24 mmol) was added dropwise. The reaction mixture was allowed to warm to rt over 1 h. Sat. aq NH4Cl was added and the mixture was extracted three times with Et2O. The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (10:1 hept-EA to 1:2) gave the title compound as a pale yellow oil. TLC: rf (50:50 hept-EA)=0.21.

Provenance & Evidence