Trichloroacetonitrile → HCID 57545958, compound

Participants

Reaction Conditions

Reaction Steps

(±)-1-(1-(Cyclopropylmethyl)-6-(trifluoromethyl)-1H-benzo[d]imidazol-4-yl)ethanol (0.283 g, 0.996 mmol) was dissolved in diethyl ether (13 mL), cooled to 0° C. and treated with 1,8-diazabicyclo(5.4.0)undec-7-ene (341 μL, 2.27 mmol). The reaction was stirred for 10 min and treated with trichloroacetonitrile (300 μL, 2.93 mmol) dropwise over 10 min. The reaction was allowed to warm up to room temperature overnight and concentrated. Flash chromatography on silica gel (50% ethyl acetate/hexanes) gave 195 mg (45.6%) as an light yellow oil. 1H-NMR (500 MHz, CHLOROFORM-D) δ ppm 8.33 (s, 1 H), 8.15 (s, 1 H), 7.69 (s, 1 H), 7.64 (s, 1 H), 6.81 (q, J=6.4 Hz, 1 H), 4.05 (d, J=7.0 Hz, 2 H), 1.82 (d, J=6.4 Hz, 3 H), 1.29-1.39 (m, 1 H), 0.70-0.80 (m, 2 H), 0.40-0.50 (m, 2 H); 19F-NMR (470 MHz, CHLOROFORM-D) δ ppm −61.19.

Provenance & Evidence