Dimethylformamide → HCID 22490569, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-ethoxycarbonylamino-4-iodobenzotrifluoride (1.8 g), 2,5-dihydro-2,5-dimethoxyfuran (1.3 g), palladium acetate (60 mg), diisopropylethylamine (2.0 g), benzyltriethylammonium chloride (1.2 g) and DMF (15 ml) was stirred for 20 hours under a nitrogen atmosphere at 80° C. Water and ethyl acetate were added to the reaction mixture, the insoluble portion was filtered out with celite, and extraction was performed with ethyl acetate. The organic layer was collected and dried over sodium sulfate and then concentrated under reduced pressure. Dichloromethane (25 ml) and trifluoroacetic acid (1.5 ml) were added to the obtained residue, and the mixture was stirred at room temperature for 2 hours. Saturated sodium bicarbonate water was added to the reaction mixture and vigorously stirred therewith. The organic layer was collected and dried over sodium sulfate and then concentrated under reduced pressure. A (1-ethoxycarbonyl-6-trifluoromethyl-1H-indol-3-yl)acetic acid methyl ester component was purified from the obtained residue by silica gel column chromatography using a mixed solvent of hexane and ethyl acetate. A 2 N sodium hydroxide aqueous solution (1 ml) and methanol (1 ml) were added to the obtained (1-ethoxycarbonyl-6-trifluoromethyl-1H-indol-3-yl)acetic acid methyl ester, and the mixture was heated to reflux for one hour. Water was added to the reaction mixture, which was then rendered acidic with concentrated aqueous hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure, to obtain 77 mg of the title compound as a colorless powder (5% yield).

Provenance & Evidence