Trichloroacetonitrile → HCID 57546209, compound

Participants

Reaction Conditions

Reaction Steps

(±)-1-(3-Bromo-5-(trifluoromethyl)-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-7-yl)ethanol (1.07 g, 2.44 mmol) was dissolved in diethyl ether (10 mL), cooled to 0° C. and treated with 1,8-diazabicyclo(5.4.0)undec-7-ene (70 μL, 0.49 mmol). The reaction was stirred for 10 min and treated with trichloroacetonitrile (370 μL, 3.65 mmol) dropwise over 10 min. The reaction was allowed to warm to room temperature overnight and concentrated. Flash chromatography on silica gel (5% ethyl acetate/hexanes) gave 1.29 g (91%) as an oil. 1H-NMR (CDCl3, 300 MHz) δ 8.25 (s, 1H), 7.86 (s, 1H), 6.66 (q, J=6.6 Hz, 1H), 6.27 (d, J=11.7 Hz, 1H), 5.68 (d, J=11.7 Hz, 1H), 3.52-3.59 (m, 2H), 1.77 (d, J=6.6 Hz, 3H), 0.82-0.87 (m, 2H), 0.05 (s, 9H).

Provenance & Evidence