Toluene → 1-Benzyl-6-phenyl-1H-indole

Participants

Reaction Steps

1-Benzyl-6-phenyl-1H-indole was prepared by coupling 1-benzyl-6-bromo-1H-indole (3.48 g, 12.2 mmol), and phenylboronic acid (1.63 g, 13.4 mmol), using tetrakis(triphenylphosphine) palladium (0.976 g, 0.846 mmol), and sodium carbonate (5.2 g, 49 mmol) in water (25 mL), ethanol (5 mL), and toluene (55 mL), according to the procedure described in Step 2 of Example 2. Purification by flash chromatography using 0-2.5% ethyl acetate in hexane as an eluant afforded the title compound as a light green solid (2.02 g, 58%), mp: 109-110° C. Mass spectrum (+ES, [M+H]+) m/z 284; 1HNMR (500 MHz, DMSO-d6): δ 7.75(s, 1H), 7.6-7.65 (m, 3H), 7.55 (d, 1H, J=3.1 Hz), 7.45 (t, 2H, J=7.5 Hz), 7.3-7.35 (m, 4H), 7.2-7.25 (m, 3H), 6.5 (d, 1H, J=3.0 Hz), and 5.5 ppm (s, 2H). Elemental Analysis for C21H17N: Calculated: C, 89.01; H, 6.05; N, 4.94. Found: C, 89.04; H, 5.87; N, 4.79.

Provenance & Evidence