3-(Trifluoromethyl)aniline → 5-Chloro-2-(3-((3-(trifluoromethyl)phenyl)amino)azetidin-1-yl)nicotinic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(Trifluoromethyl)aniline (0.047 ml, 0.374 mmol) in acetonitrile (0.5 ml), potassium carbonate (67.21 mg, 0.486 mmol) was added followed by the addition of methyl 5-chloro-2-(3-((methylsulfonyl)oxy)azetidin-1-yl)nicotinate (D63)(120 mg, 0.374 mmol). The reaction mixture was heated at 160° C. under microwave irradiation for 25 min. Lithium hydroxide monohydrate (23.54 mg, 0.561 mmol) was added and the resulting reaction mixture was heated at 150° C. under microwave irradiation for 5 min. Solvents were evaporated in vacuo and the residue was diluted with water (5 ml) and HCl 1M (15 ml) and extracted with ethyl acetate (3×20 ml). Collected organics, after solvent evaporation, afforded the title compound (D115) (50 mg)

Provenance & Evidence