1-benzyl-4-[4-(trifluoromethoxy)phenyl]-1H-indole was prepared by coupling 1-benzyl-4-bromo-1H-indole (0.787 g, 2.75 mmol), and 4-trifluoromethoxyphenylboronic acid (0.683 g, 3.32 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.0679 g, 0.0831 mmol), and potassium carbonate (0.575 g, 4.16 mmol) in dioxane (21 mL) and water (2.1 mL) following the procedure described in Step 1 of Example 11. Purification by HPLC using hexane as the mobile phase yielded the title compound as a light yellow gum (0.246 g, 24%). 1HNMR (300 MHz, DMSO-d6): δ 7.75 (d, 2H, J=8.3 Hz), 7.65 (d, 1H, J=2.3 Hz), 7.45-7.55 (m, 3H), 7.1-7.4 (m, 7H), 6.6 (d, 1H, J=2.3 Hz), and 5.45 ppm (s, 2H).
