Potassium Carbonate → HCID 11020512, compound

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Reaction Steps

0.73 g of 2-methoxyphenylboronic acid and then 1.66 g of potassium carbonate are successively added to a solution of 0.78 g of 4-bromoindole in 15 ml of dioxane and 5 ml of water under argon. The reaction mixture is stirred at ambient temperature for 15 minutes, and then 0.16 g of dichlorobis(tri-o-tolylphosphine)palladium(II) is added. The reaction mixture is stirred at ambient temperature for 16 hours, and then at 60° C. for 18 hours, and, finally, at 110° C. for 3 hours. After returning to ambient temperature, the mixture is concentrated to dryness under reduced pressure. The residue is taken up in a mixture of 15 ml of a 2N sodium hydroxide solution and 30 ml of ethyl acetate. The mixture is filtered through Clarcel®, and then separated by settling out. The organic phase is separated and the aqueous phase is extracted with 2×30 ml of ethyl acetate. The organic phases are combined, dried over anhydrous magnesium sulfate, filtered, and then concentrated to dryness under reduced pressure. The residue is purified on a 30 g cartridge of 15-40 μm silica, elution being carried out with a 60/40 v/v cyclohexane/dichloromethane mixture, at a flow rate of 30 ml/min. 0.44 g of 4-(2-methoxyphenyl)indole is thus obtained in the form of a pale yellow solid, the characteristics of which are the following:

Provenance & Evidence