Sodium Carbonate → 5-(4-chlorophenyl)-3-(1-methylpiperidin-4-yl)-1H-indole

Participants

Reaction Steps

The title compound was prepared by the procedure of Example 10, beginning with 5-bromo-3-(1-methylpiperidin-4-yl)-1-(triisopropylsilyl)-indole (0.500 g, 1.11 mmol), 4-chlorophenylboronic acid (0.183 g, 1.17 mmol), tetrakis(triphenylphosphine)palladium(0) (0.064 g, 0.056 mmol), and 2M aqueous sodium carbonate solution (2 mL) in toluene (15 mL) to give 0.200 g of 5-(4-chlorophenyl)-3-(1-nethylpiperidin-4-yl)-1-(triisopropylsilyl)-indole (40%) as a white solid, which was desilylated by dissolving in 1 mL of tetrahydrofuran and treating with tetrabutylammonium fluoride (1M in tetrahydrofuran, 4 mL) to give the title compound (0.112 g, 83%) as an amorphous solid. FDMS m/e=325 (M+). EA calculated for C20H21N2Cl.½ H2O: C, 71.95; H, 6.64; N, 8.39. Found: C, 72.09; H, 6.68; N, 8.48.

Provenance & Evidence