Potassium Carbonate → tert-butyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1-methyl-1H-indole-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl 2-bromo-3-cyclohexyl-1-methyl-1H-indole-6-carboxylate (24, 500 mg, 1.27 mmol), 2-hydroxy-phenylboronic acid (211 mg, 1.53 mmol) and potassium carbonate (1.35 g, 12.74 mmol) in 100 mL of 1,2-dimethoxyethane/water (4:1) was thoroughly flushed with argon. Then trans-bis(triphenylphosphine)palladium(II) chloride (0.147 g, 0.127 mmol) was added and the reaction was heated at 100° C. under argon for 12 h. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethylacetate (EtOAc). 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 tert-butyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1-methyl-1H-indole-6-carboxylate 25: m/z=406 (M+H)+.

Provenance & Evidence