Indole → HCID 11658322, compound

Participants

Reaction Steps

To a solution of indole (0.50 g, 4.67 mmol), zinc trifluoromethanesulfonate (1.02 g, 2.8 mmol) and tetrabutylammonium iodide (0.86 g, 2.34 mmol) in toluene (14 mL) was added N,N-diisopropylethylamine (0.89 mL, 5.14 mmol) and the mixture was stirred at room temperature for about 15 min. Propargyl bromide (0.26 mL, 2.34 mmol) was added and the solution was stirred at room temperature for about 4 hours. The solution was quenched by addition of aqueous ammonium chloride and the mixture was extracted with diethyl ether. The combined organic extracts were dried (MgSO4), filtered and concentrated under vacuum, the residue was purified by flash column chromatography on silica gel using hexanes/ethyl acetate (8:1) as the mobile phase to provide Example 650. 1H NMR (300 MHz, CDCl3) δ 2.13 (t, J=2.7 Hz, 1H), 3.70 (d, J=2.7 Hz, 2H), 6.55 (s, 1H), 7.37 (m, 2H), 7.64 (m, 2H), 7.98 (br s, 1H).

Provenance & Evidence