Tetrahydrofuran → HCID 86606804, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 3-chloro-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridine (i.e. the pyrazole product from Step A) (2.72 g, 11.14 mmol) in tetrahydrofuran (50 ml) was cooled to −70° C. Lithium diisopropylamine (2M in THF/Heptane, 5.5 mL, 11.0 mmol) was added over 2 minutes and the mixture was stirred for 15 minutes. 2-Chloro-6-methylphenyl isocyanate (1.90 g, 11.33 mmol) was added via syringe. The mixture was allowed to warm to 20° C. and quenched with a saturated aqueous solution of ammonium chloride (50 mL). The reaction mass was extracted with ethyl acetate (100 mL), dried over magnesium sulfate and concentrated. Chromatography on silica gel with a gradient of 3:1 hexanes/ethyl acetate to 1:1 hexanes/ethyl acetate afforded the title compound, a compound of the present invention as a solid (3.0 g) melting at 212-213° C.

Provenance & Evidence