Fluorine → HCID 58374107, compound

Participants

Reaction Steps

The synthetic intermediate imine (Z)-2,2,2-trifluoro-N-(pyridin-2-yl)acetimidoyl chloride was prepared as described in Huang et al., J. Fluorine Chem., 74:279-282 (1995) and used without distillation. To ethyl isocyanoacetate (0.543 g, 4.8 mmol) in dry THF (50 mL) was added NaH (192 mg, 4 8 mmol, 60% dispersed in oil) at 0° C. and after 5 minutes, (Z)-2,2,2-trifluoro-N-(pyridin-2-yl)acetimidoyl chloride (1.0 g, 4.8 mmol) in 50 mL THF. The reaction mixture was allowed to warm to room temperature and then purified using an 80 g SiO2 column and a 50-100% EtOAc/hexanes gradient. The product eluted to yield 1.23 g (90% yield) of ethyl 1-(pyridin-2-yl)-5-(trifluoromethyl)-1H-imidazole-4-carboxylate as a yellow oil. MS (M+1)=286.1; HPLC RT=1.08 minutes.

Provenance & Evidence