Ethanamine, 2,2,2-trifluoro- → 1-[3-Chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropanecarbonitrile

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Reaction Steps

1.4 g 1-(3-chloro-5-vinyl-2-pyridyl)cyclopropanecarbonitrile (step 1) was dissolved in 2.0 ml toluene and 14 mg 5,10,15,20-tetraphenyl-21H,23H-porphine iron(III) chloride was added. Then 30 ml water was added, followed by 1.4 g 2,2,2-trifluoroethanamine and 1.1 g sodium nitrite. The reaction mixture was stirred for 3 hours at ambient temperature. Then saturated ammonium chloride solution was added and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated. Crude material was obtained as a dark oil, which was purified by flash chromatography on silica gel with heptane/ethyl acetate as a solvent. Thus, 1.2 g of 1-[3-chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropanecarbonitrile was obtained as a brown oil. 1H-NMR (CDCl3): 8.25 ppm (s, 1H), 7.44 ppm (s, 1H), 2.35 ppm (m, 1H), 1.85 ppm (m, 1H), 1.75 ppm (m, 2H), 1.60 ppm (m, 2H), 1.50 ppm (m, 1H), 1.24 ppm (m, 2H).

Provenance & Evidence