4-Nitrophenol → HCID 58733604, compound

Participants

Reaction Steps

A homogeneous brown solution of (6-chloro-3-cyano-5-fluoro-pyridin-2-yl)-acetic acid (2.37 g, 11.0 mmol), as prepared in the previous step, 4-nitrophenol (1.84 g, 13.2 mmol), and DCM (11 mL) was stirred under argon at 0° C. while 1,3-diisopropylcarbodiimide (DIC) (1.90 mL, 12.1 mmol) was added dropwise with stirring over 3 min. The ice bath was immediately removed following completion of the DIC addition, and the brown mixture with yellowish precipitate was stirred at rt for 1 h 40 min. The crude reaction was then directly loaded onto a flash silica column and eluted with 96:4 toluene/CH3CN to afford the title compound as a translucent pale yellow oil (3.11 g, 84%). 1H-NMR (300 MHz, CDCl3) δ 8.29 (m, 2H), 7.80 (d, 1H), 7.35 (m, 2H), 4.35 (d, 0.7 Hz, 2H).

Provenance & Evidence