Citric Acid → HCID 58306940, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-{(1S)-1-[({1-[(6-chloropyridin-3-yl)methyl]-1H-indol-7-yl}carbonyl)amino]ethyl}benzoic acid (0.15 g), phenylboronic acid (84 mg), tripotassium phosphate (0.22 g), palladium (II) chloride (9.2 mg), and biphenyl-2-yl(dicyclohexyl) phosphine (36 mg) were added dioxane (6.0 mL), water (1.5 mL), followed by stirring at 100° C. for 1 hour. The reaction mixture was adjusted to pH 3 by adding a 10% aqueous citric acid solution. The mixed liquid was filtered through Celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/THF=2/1-1/1) to obtain 4-{(1S)-1-[({1-[(6-phenylpyridin-3-yl)methyl]-1H-indol-7-yl}carbonyl)amino]ethyl}benzoic acid (66 mg).

Provenance & Evidence