2-Fluoropyridine → Tert-butyl 3-cyano-3-(pyridin-2-yl)azetidine-1-carboxylate

Participants

Reaction Steps

A solution of 2-fluoropyridine (2.6 mL, 30.2 mmol) and tert-butyl 3-cyanoazetidine-1-carboxylate (I-1, 5.0 g, 27.5 mmol) in THF (200 mL) at room temperature was treated with LHMDS (55 mL of a 1.0 M solution in THF, 55 mmol). After 6 h, the reaction mixture was poured into saturated aqueous NH4Cl (200 mL) and extracted with EtOAc (3×150 mL). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure to afford tert-butyl 3-cyano-3-pyridin-2-ylazetidine-1-carboxylate (I-2) as a yellow-brown oil. Analytical LCMS: single peak (214 nm), 3.004 min. This material was used in subsequent reactions without further purification.

Provenance & Evidence