2-Chloro-1,1,1-triethoxyethane → 2-chloromethyl-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile

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Reaction Steps

3,4-Diamino-6-(4-ethoxy-3-trifluoromethyl-phenyl)-pyridine-2-carbonitrile (1 g, 3.1 mmol) was dissolved in acetonitrile (20 ml) and ytterbium triflate (38 mg, 0.062 mmol) and 2-chloro-1,1,1-triethoxyethane (1.83 g, 9.3 mmol) were added. The mixture was heated to reflux overnight. Mixture was evaporated under reduced pressure, partitioned between ethyl acetate (100 ml) and water (100 ml), and organics were dried then evaporated under reduced pressure to afford a dark brown oil. Triturated with DCM (50 ml) to afford 495 mg of 2-chloromethyl-6-(4-ethoxy-3-trifluoromethyl-phenyl)-1H-imidazo[4,5-c]pyridine-4-carbonitrile as a light brown solid. 1H NMR (DMSO) δ 8.47-8.33 (m, 3H), 7.41 (d, 1H), 5.05 (s, 2H), 4.26 (q, 2H), 1.38 (t, 3H). MS m/z 381.1 (M+1).

Provenance & Evidence