Iodine → HCID 57678947, compound

Participants

Reaction Steps

Triiodide synthesis: Into a round bottom flask, KI (5.00 g, 30.1 mmol) was mixed with I2 (5.1 g, 20.0 mmol) in 20 mL water. The mixture was stirred at room temperature for 24 hours. To a solution of 5-methoxyindole (10, 200 mg, 1.36 mmol) and thiourea (110 mg, 1.44 mmol) in methanol (10 mL), triiodide, freshly prepared from the previous day (440 mg, 1.5 mmol) was added over a 20 minute period, and the combined mixture stirred at room temperature for 40 min. The solvent was reduced to half of its volume and 10 N NaOH (5 mL) was added to the flask and heated at 95° C. for one hour under an inert atmosphere. The resulting suspension was filtered hot and the solid rinsed with water. Filtrate was cooled to room temperature and bromoacetic acid methyl ester (241 mg, 1.6 mmol) was added. This mixture was stirred vigorously for an hour and the organic layer was extracted with diethyl ether. The aqueous layer was acidified with 1 N HCl and extracted with ether. The desired product was isolated after flash silica column chromatography using gradient solvent 5-10% EtOAc/hexane. (15 mg, 4.4%)

Provenance & Evidence