Benzo(B)Thiophene-2-Boronic Acid → 5-(2-Benzo[b]thienyl)-3-(1-methylpiperidin-4-yl)-1-(triisopropylsilyl)-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 (0.700 g, 1.56 mmol), benzo[b]thiophene-2-boronic acid (0.336 g, 1.87 mmol), tetrakis(triphenylphosphine)palladium(0) (0.090 g, 0.078 mmol), and 2M aqueous sodium carbonate solution (3 mL) in toluene (15 mL) to give 0.160 g of 5-(2-benzo[b]thienyl)-3-(1-methylpiperidin-4-yl)-1-(triisopropylsilyl)-indole (22%) as a solid, which was desilylated by dissolving in 1 mL of tetrahydrofuran and treating with tetrabutylammonium fluoride (1M in tetrahydrofuran, 7 mL) to give the title compound (0.048 g, 43%) as an amorphous solid. FDMS m/e=346 (M+). EA calculated for C22H22N2S.¼ H2O: C, 75.28; H, 6.46; N, 7.98. Found: C, 75.11; H, 6.84; N, 7.91.

Provenance & Evidence