Hydrochloric Acid → 1-benzyl-6-(3-chlorophenyl)-1H-indole

Participants

Reaction Conditions

Reaction Steps

3-Chlorophenylboronic acid (1.21 g, 7.76 mmol) was added in four portions to the mixture of 1-benzyl-6-bromo-1H-indole (1.12 g, 3.91 mmol), palladium (II) acetate (0.0191 g, 0,0850 mmol), and tetrabutylammonium bromide (1.26 g, 3.91 mmol) in water (22.5 mL) and THF (2.5 mL) while heating at 70° C. for 4 hours. The reaction mixture was allowed to cool to room temperature and 2N hydrochloric acid was slowly added. The mixture was extracted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography (Biotage apparatus) using 0-100% ethyl acetate in hexane as an eluant. Drying at 60° C. for 40 minutes yielded (0.621 g, 50%) of 1-benzyl-6-(3-chlorophenyl)-1H-indole as a yellow gum. Mass spectrum (+ESI, [M+H]+) m/z 318; 1HNMR (500 MHz, DMSO-d6): δ 7.85 (s, 1H), 7.75 (t, 1H, J=1.8 Hz), 7.6-7.65 (m, 2H), 7.55(d, 1H, J=3.1 Hz), 7.45 (t, 1H, J=7.8 Hz), 7.25-7.35 (m, 4H), 7.2-7.25 (m, 3H), 6.5 (d, 1H, J=3.1 Hz), and 5.5 ppm (s, 2H). Elemental Analysis for C21H16ClN: Calculated: C, 79.36; H, 5.07; N, 4.41. Found: C, 79.32; H, 5.21; N, 4.28.

Provenance & Evidence