Aniline → HCID 23152808, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl 2-bromo-3-cyclohexyl-1-(2-ethoxycarbonylethyl)-1H-indole-6-carboxylate (1.00 g, 2.29 mmol) and 2-dioxaborolan-2-yl)phenylamine (697 mg, 2.75 mmol) in 1,2-dimethoxyethane (12 ml) and water (6 ml) were added lithium chloride (291 mg, 6.87 mmol), sodium carbonate (729 mg, 6.87 mmol) and tetrakis(triphenyl)phosphine)palladium (265 mg, 0.229 mmol), and the mixture was stirred at 90° C. for 3.5 hr. The mixture was allowed to cool to room temperature and saturated aqueous ammonium chloride solution and ethyl acetate were added. The mixture was filtered through celite, and the filtrate was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (hexane:acetone=3:1) to give methyl 2-(2-amino-4-chlorophenyl)-3-cyclohexyl-1-(2-ethoxycarbonylethyl)-1H-indole-6-carboxylate (1.10 g, yield 100%).

Provenance & Evidence