Potassium tert-butoxide → 4-Bromo-6-(trifluoromethyl)-1H-indole

Beteiligte Stoffe

Reaktionsschritte

A solution of 3-bromo-2-ethynyl-5-(trifluoromethyl)aniline (7.54 g, 28.6 mmol) in N-methylpyrollidinone (50 mL) was added dropwise to a 0° C. solution of potassium tert-butoxide (6.41 g, 57.1 mmol) in N-methylpyrollidinone (200 mL). The reaction was stirred at ambient temperature for 4 h. The reaction was poured into brine (500 mL) and extracted with ethyl acetate (4×50 mL). The combined organic layers were washed with brine (100 mL), dried with magnesium sulfate and evaporated. The residue was purified by chromatography on silica gel with a gradient of 10% to 25% ethyl acetate/hexanes to give 7.16 g (95%) as a brown oil. 1H-NMR (CDCl3, 400 MHz) δ 8.54 (bs, 1H), 7.63 (s, 1H), 7.53 (s, 1H), 7.40 (t, J=2.8 Hz, 1H), 6.66 (t, J=2.8 Hz, 1H); LC/MS (HPLC method 4): tR=3.280 min, 264.12(MH)+.

Herkunft & Nachweise