Potassium Carbonate → methyl 2-[2-(benzyloxy)phenyl]-3-cyclohexyl-1H-indole-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate (1, 6.14 g, 18.3 mmol), 2-(benzyloxy)phenylboronic acid (5.00 g, 21.9 mmol) and potassium carbonate (5.80 g, 42 mmol) in 450 mL of 1,2-dimethoxyethane/water (4:1) was thoroughly flushed with argon. Then trans-BIS(triphenylphosphine)palladium(II) chloride (0.641 g, 0.91 mmol) was added and the reaction was heated at 70° C. under argon for 12 h. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethylacetate (AcOEt). Combined organic layers were washed with a saturated solution of NaHCO3 and brine, dried over anhydrous Na2SO4 and filtered. The filtered solution was concentrated under vacuum to give methyl 2-[2-(benzyloxy)phenyl]-3-cyclohexyl-1H-indole-6-carboxylate 2: m/z=440 (M+H)+. Step 2

Provenance & Evidence