Bromine → HCID 23114120, compound

Participants

Reaction Steps

To a mixture of N-(3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzothien-5-yl)-3,3-dimethylbutanamide (560 mg, 1.41 mmol) obtained in Example 161 and iron powder (5.2 mg, 0.094 mmol) in dichloromethane (10 mL) was added bromine (225 mg, 1.41 mmol) at 0° C. and the resulting mixture was stirred at the same temperature for 1 hour. Water was poured into the reaction mixture and the product was extracted with ethyl acetate. The extracts were washed with an aqueous sodium hydrogen carbonate solution and water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. To a mixture of the obtained residue and sodium hydrogen carbonate (150 mg, 1.79 mmol) in dichloromethane (5 mL) was added m-chloroperbenzoic acid (161 mg, 1.01 mmol) at 0° C. and the resulting mixture was stirred at room temperature for 1 hour. To the reaction solution was added an aqueous sodium hydrogensulfite solution, the organic layer was separated, and the aqueous layer was extracted with dichloromethane. The combined organic layers were washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane ethyl acetate=3:1) to obtain 393 mg (yield: 55%) of the title compound. Melting point: 211-213° C. (hexane-ethyl acetate).

Provenance & Evidence