Pyridine → HCID 67128641, compound

Participants

Reaction Steps

To a suspension of methyl 4-carbamoyl-2-chloro-6-fluorobenzoate (2.527 g, 10.9 mmoles) in 1,4-dioxane (25 mL) at room temperature was added pyridine (38.2 mmoles, 3.02 g), followed by trifluoroacetic anhydride (5.04 g, 24.0 mmoles). The reaction mixture was stirred at room temperature for 2 hours. The reaction was quenched with water (100 mL), extracted with EtOAc (3×100 mL). The combined organics were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-15% EtOAc/hexane) to afford methyl 2-chloro-4-cyano-6-fluorobenzoate as a white solid (1.953 g, yield: 84%). 1H NMR (400 MHz, CDCl3) δ 7.55 (d, J=1.1 Hz 1H), 7.37 (dd, J=8.0, 1.2 Hz, 1H), 4.00 (s, 3H). LCMS (APCI+) 214.0 [M+H]+.

Provenance & Evidence