4-(Trifluoromethyl)phenyl isocyanate → HCID 25252969, compound

Participants

Reaction Steps

A solution of (R)-tert-butyl 2-(4-(4-chlorobenzyl)-1-methyl-1H-pyrazol-3-yl)pyrrolidine-1-carboxylate (39 mg, 0.1 mmol) was dissolved in 4M HCl in 1,4-dioxane (2 mL), stirred for 2 hr and then concentrated in vacuo. The resulting residue was then suspended in dichloromethane (2 mL) and DIEA (34 μL, 0.2 mmol) before 1-isocyanato-4-(trifluoromethyl)benzene (28 μL, 0.15 mmol) was added. After 16 h of stirring, the reaction mixture was concentrated in vacuo. Purification of the resulting residue by silica gel column chromatography (hexanes/ethyl acetate gradient, 10-100% EtOAc) afforded (R)-2-(4-(4-chlorobenzyl)-1-methyl-1H-pyrazol-3-yl)-N-(4-(trifluoromethyl)phenyl)pyrrolidine-1-carboxamide (12 mg, 26%).

Provenance & Evidence