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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
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1,2-Dichloroethane | HCID 11 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amine | HCID 10954023 | — |
| 反応物 | (e)-3-(2-Oxo-2,3-dihydro-1h-indol-5-yl)acrylic acid hydrochloride salt | HCID 66905016 | — |
| 反応物 | HCID 178526939 | HCID 178526939 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | (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% |
反応手順
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)+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07250424B2 |
| 出典データセット | uspto-grants-2007_07 |
| ORD ID | ord-481e49e6a0434aaa97c42162fd970bd6 |
| 出典メモ | uspto-grants-2007_07 |