2-Bromopyridine → HCID 67376913, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (1.0 g, 5.10 mmol, Aldrich) in 1,4-dioxane (10 mL) in a sealed tube was treated with 2-bromopyridine (0.40 g, 2.50 mmol, Aldrich) and heated at 150° C. for 12 hours. The mixture was allowed to cool to room temperature and was concentrated under reduced pressure. The residue was purified by flash chromatography (5% MeOH/CH2Cl2) to provide the title compound. 1H NMR (CDCl3, 300 MHz) δ 1.48(m, 9H), 1.86–1.94(m, 2H), 3.30–3.58(m, 4H), 4.52(brs, 0.5H), 4.67(brs, 0.5H), 4.80(brs, 0.5H), 4.92(brs, 0.5H), 6.32(d, J=9.0 Hz, 1H), 6.57(t, J=6.0 Hz, 1H), 7.38–7.55(m, 1H), 8.12(d, J=6.0 Hz, 1H). MS (DCI/NH3) m/z 276 (M+H)+.

Provenance & Evidence