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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1514959Generated: November 3, 2026

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-indol-2-yl]-3,5-dimethylphenyl}-propionic acid methyl ester

https://huagongshe.com/reaction/1514959

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
Reactant4-Tert-ButylanilineHCID 69861—
Reactant1-HydroxybenzotriazoleHCID 75771—
Reactant2-[4-(2-Methoxycarbonylethyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylic acidHCID 66966205—
SolventTetrahydrofuranHCID 8028—
Product3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-indol-2-yl]-3,5-dimethylphenyl}-propionic acid methyl esterHCID 66966000—

Reaction Conditions

Temperature150 °C

Reaction Steps

A mixture of 2-[4-(2-methoxycarbonylethyl)-2,6-dimethylphenyl]-1H-indole-6-carboxylic acid (100 mg, 280 μmol), 4-tert-butylaniline (45 μL, 290 μmol), EDCI (82 mg, 430 μmol) and HOBT (42 mg, 310 μmol) in THF (10 mL) was heated in a microwave apparatus at 150° C. for 3 h. The solvent was removed under reduced pressure and the residue was chromatographed using a 10-60% gradient of heptane/ethyl acetate to give 3-{4-[6-(4-tert-butylphenylcarbamoyl)-1H-indol-2-yl]-3,5-dimethylphenyl}-propionic acid methyl ester. MS (m/z) 484.3 (M+1); Retention time=1.50 min (Method 10).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08222248B2
Source datasetuspto-grants-2012_07
ORD IDord-feb4078d47484e6c8533c345e239c38e
Source noteuspto-grants-2012_07