Sodium Cyanide → 7-Chloro-3-(2,2,2-trifluoroethyl)imidazo[1,2-a]pyridine-8-carbonitrile

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Reaction Steps

A 2.0-5.0 mL microwave vial was charged with 7-chloro-8-iodo-3-(2,2,2-trifluoroethyl)imidazo[1,2-a]pyridine (50 mg, 0.139 mmol) and dissolved in DMF (1387 μl). To that stirring solution was added sodium cyanide (7.14 mg, 0.146 mmol) followed by copper(I) iodide (39.6 mg, 0.208 mmol). The vial was sealed and degassed using ultra pure argon and sonication for 2 min. The vial was then placed in a reaction block preheated to 120° C. After 2 hours, LCMS showed ˜7.5:1 (product:starting material). The mixture was diluted with EtOAc and sat'd sodium bicarbonate and the contents of the flask were transferred into a separatory funnel where the aqueous was extracted twice with EtOAc and discarded. The combined organics were washed with brine, dried with magnesium sulfate, and concentrated under reduced pressure. The crude was taken on into a coupling reaction without any further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.95 (d, J=7.3 Hz, 1H), 7.78 (s, 1H), 7.43 (d, J=7.5 Hz, 1H), 4.30 (q, J=11.0 Hz, 2H).

Provenance & Evidence