HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 4-{5-[(E)-2-Ethoxycarbonylvinyl]-3-cyanoindol-1-yl}benzoic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acrylate | HCID 8821 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 4-(5-Bromo-3-cyanoindol-1-yl)benzoic acid ethyl ester | HCID 25052346 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-{5-[(E)-2-Ethoxycarbonylvinyl]-3-cyanoindol-1-yl}benzoic acid | HCID 66617361 | 35.9% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08829040B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-9bfa10632c524d74b4db70100f8cc46f |
| Source note | uspto-grants-2014_09 |