Water → HCID 59200416, compound

Participants

Reaction Steps

To a cold (−78° C.), stirred solution of 2-bromopyridine (0.38 mL, 4.0 mmol) in THF (40 mL) under Ar was added dropwise t-BuLi (5.2 mL, 8.8 mmol). After 30 min, 2-aminoacetophenone•HCl (687 mg, 4.00 mmol) was added as a solid in one portion. The reaction was allowed to slowly warm to RT as the bath warmed. Water was added and the reaction mixture was extracted with EtOAc, dried (MgSO4), filtered and concentrated to afford a solid. Purification by flash chromatography afforded 68 mg as an oil: 1H NMR (400 MHz, CDCl3) δ ppm 8.50 (d, J=4.80 Hz, 1H), 7.70-7.19 (m, 8H), 3.72 (d, J=13.14 Hz, 1H), 3.38 (d, J=13.14 Hz, 1H).

Provenance & Evidence