Triethylamine → methyl 2-(5,6-dimethoxy-1H-indene-2-carboxamido)benzoate

関与物質

反応手順

To a stirred mixture of 5,6-dimethoxy-1H-indene-2-carboxylic acid (230 mg, 1.05 mmol) and DMF (20 μL) in DCM (10 mL) was added oxalyl chloride (267 mg, 2.10 mmol) dropwise at room temperature. The resulting mixture was stirred for 2 hours then concentrated and dried under high vacuum. The resulting acid chloride was then taken up into DCM (10 mL) and added dropwise to a stirred mixture of methyl 2-aminobenzoate (174 mg, 1.16 mmol) and triethylamine (159.1 mg, 1.58 mmol) in DCM (10 mL) 0° C. The mixture was then stirred overnight at room temperature before adding water and extracting with DCM. The organic extracts were dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography with petroleum ether/ethyl acetate 5:1 (v:v) as eluent to give methyl 2-(5,6-dimethoxy-1H-indene-2-carboxamido)benzoate (140 mg, 38%). LC-MS (ES-API); rt 9.35 min; m/z calculated for C20H19NO5 [M+H]+ 354.1, found 354.1.

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