Potassium Phosphate, Tribasic → 3-Cyclopropyl-1-triisopropylsilanyl-1H-indole

Participants

Reaction Steps

Dissolve 3-bromo-1-triisopropylsilanyl-1H-indole (1.02 g, 2.89 mmol), cyclopropylboronic acid (259 mg, 3.01 mmol) and K3PO4 (1.8 g, 8.5 mmol) in a mixture of toluene (20 mL) and water (0.8 mL). Add tricyclohexyl-phosphane (86 mg, 0.31 mmol) and palladium(II) acetate (50 mg, 0.22 mmol) and stir the mixture at 70° C. for 3 h. Filter the mixture through celite and wash the solids with EtOAc (30 mL). Collect and concentrate the filtrate and purify the residue by flash chromatography, using a linear gradient of 100% hexanes to 10% EtOAc/hexanes, to give the title compound as a clear oil 765 mg (84%): MS (ES) 314.1 (M+1)+.

Provenance & Evidence