2-Bromopyridine → HCID 9882417, compound

Participants

Reaction Steps

To a dry 25 mL reaction flask was added 2-bromopyridine (200 mg, 1.3 mmol) dissolved in CH2Cl2 (3 mL) and the temperature was adjusted to −78° C. After being stirred for 20 min, addition of n-BuLi (0.84 mL, 1.4 mmol) was conducted under inert atmosphere. After additional 30 min, a solution of 23 dissolved in CH2Cl2 (2 mL) was added. The reaction mixture was left to warm to rt over-night before being quenched with H2SO4 (5 mL, 1 M). The reaction mixture was extracted with ethyl acetate (6×25 mL) and the combined organic phases were dried (MgSO4) and evaporated to dryness, to produce 0.31 g of crude 24. The crude product was subjected to CC [eluent: CH2Cl2: MEOH (10:1)] to give pure 24 (75 mg, 12%). LC-MS [M+H]+ 288 (cald. 288.2).

Provenance & Evidence