Dichloromethane → 1-Benzyl-5-phenyl-1H-indole

Participants

Reaction Steps

1-Benzyl-5-phenyl-1H-indole was prepared by coupling 1-benzyl-5-bromo-1H-indole (2.72 g, 9.50 mmol), and phenylboronic acid (1.39 g, 11.4 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.266 g, 0.326 mmol), and potassium carbonate (2.06 g, 14.9 mmol) in dioxane (72 mL) and water (7.2 mL), following the procedure described in Step 1 of Example 11. Purification by flash chromatography (Biotage apparatus) using hexane as an eluant yielded the title compound as a light yellow solid (0.928 g, 35%), mp: 105-106° C. Mass spectrum (+ES, [M+H]+) m/z 284; 1HNMR (500 MHz, DMSO-d6): δ 7.8 (d, 1H, J=0.92 Hz), 7.65 (dd, 2H, J=8.2 Hz and 0.84 Hz), 7.5-7.55 (m, 2H), 7.35-7.45 (m, 3H), 7.2-7.3 (m, 6H), 6.55 (dd, 1H, J=3.1 Hz and 0.61 Hz), and 5.45 ppm (s, 2H).

Provenance & Evidence