Hydrochloric Acid → HCID 69211145, compound

Participants

Reaction Steps

A solution of 2.15 g (4.66 mmol) of the 2,3-dihydro-1-[(4-iodophenyl)sulfonyl]-(2S)-1H-indole-2-carboxylic acid obtained according to Preparation IV(a) in 40 ml of DME is prepared and 13 ml of water are added, followed by 1.24 g (11.6 mmol) of sodium carbonate, 380 mg (0.46 mmol) of PdCl2dppf and 1.77 g (9.3 mmol) of 2-(trifluoromethyl)phenylboronic acid. The reaction medium is stirred at room temperature for 30 min and then at 90° C. for 30 min. After cooling, water is added and the medium is acidified with N hydrochloric acid. The mixture is then extracted with ethyl acetate. The organic phase obtained is washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The crude product is purified by reversed phase chromatography on RP18-grafted silica gel using an acetonitrile/water/trifluoroacetic acid mixture (8/2/0.02; v/v/v) as the eluent to give the product in the form of an orange oil (yield=80%).

Provenance & Evidence