HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
1,2-Dichloroethane → (E)-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)-3-(2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)acrylamide
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | 1,2-Dichloroethane | HCID 11 | — |
| Edukt | Diisopropylethylamine | HCID 81531 | — |
| Edukt | N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amine | HCID 10954023 | — |
| Edukt | (e)-3-(2-Oxo-2,3-dihydro-1h-indol-5-yl)acrylic acid hydrochloride salt | HCID 66905016 | — |
| Edukt | HCID 178526939 | HCID 178526939 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | (E)-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)-3-(2-oxo-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-5-yl)acrylamide | HCID 10021425 | 88% |
Reaktionsschritte
To a solution of (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylic acid hydrochloride salt (0.50 g, 2.1 mmole), hydroxybenzotriazole monohydrate (0.31 g, 2.3 mmole), diisopropylethylamine (0.80 mL, 4.6 mmole), and 2-methyl-3-(methylaminomethyl)indole (0.40 g, 2.3 mmole) in DMF (50 mL) at RT was added EDC (0.46, 2.3 mmole). After 12 hr the reaction solution was concentrated under vacuum and the residue was purified by flash chromatography on silica gel (9:1 CHCl3/CH3OH containing 5% NH4OH) to give the title compound (0.66 g, 88%) as a light yellow solid: MS (ES) m/e 361 (M+H)+.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07250424B2 |
| Quelldatensatz | uspto-grants-2007_07 |
| ORD ID | ord-481e49e6a0434aaa97c42162fd970bd6 |
| Quellennotiz | uspto-grants-2007_07 |