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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 73361Generated: October 31, 2026

Triethylamine → 4-{5-[(E)-2-Ethoxycarbonylvinyl]-3-cyanoindol-1-yl}benzoic acid

https://huagongshe.com/reaction/73361

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantEthyl AcrylateHCID 8821—
ReactantTriphenylphosphineHCID 11776—
Reactant4-(5-Bromo-3-cyanoindol-1-yl)benzoic acid ethyl esterHCID 25052346—
Catalystpalladium(II) acetateHCID 167845—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product4-{5-[(E)-2-Ethoxycarbonylvinyl]-3-cyanoindol-1-yl}benzoic acidHCID 6661736135.9%

Reaction Steps

A solution of 4-(5-bromo-3-cyanoindol-1-yl)benzoic acid ethyl ester (0.1 g), acrylic acid ethyl ester (0.11 g) and triethylamine (0.082 g) in N,N-dimethylformamide (2 mL) was stirred in the presence of palladium (II) acetate (0.0061 g) and triphenylphosphine (0.014 g) at 100° C. for 30 hours. This reaction mixture was poured into water, and this resulting mixture was extracted with ethyl acetate twice. This organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel. (eluent: ethyl acetate/n-hexane=10/90-75/25) to give the title compound (0.035 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08829040B2
Source datasetuspto-grants-2014_09
ORD IDord-9bfa10632c524d74b4db70100f8cc46f
Source noteuspto-grants-2014_09