4-(Trifluoromethoxy)-1H-indole-2-carboxylic acid → HCID 53418161, compound

Participants

Reaction Conditions

Reaction Steps

0.18 g of copper(0) is added to a solution of 1.0 g of 4-(trifluoromethoxy)-1H-indole-2-carboxylic acid in 4.5 ml of quinoline under argon. The reaction mixture is heated at 200° C. for 5 hours, and is then cooled to ambient temperature. After dilution with 30 ml of diethyl ether, the mixture is filtered through Clarcel®. The filtrate is washed successively with 6×10 ml of a 6N hydrochloric acid solution, with 10 ml of a saturated sodium hydrogen carbonate solution and then with 10 ml of saturated brine. The organic phase is dried over anhydrous magnesium sulfate, filtered, and then concentrated to dryness under reduced pressure. The residue is purified by chromatography on a 25 g cartridge of 15-40 μm silica, elution being carried out with a 95/5 v/v cyclohexane/ethyl acetate mixture, at a flow rate of 20 ml/min. 0.33 g of 4-(Trifluoromethoxy)indole is thus obtained in the form of an amber oil, the characteristics of which are the following:

Provenance & Evidence