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tert-Butyl acrylate → tert-butyl (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | tert-Butyl acrylate | HCID 15458 | — |
| 反応物 | Tri-o-tolylphosphine | HCID 80271 | — |
| 反応物 | Diisopropylethylamine | HCID 81531 | — |
| 反応物 | 5-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one | HCID 15504062 | — |
| 触媒 | palladium(II) acetate | HCID 167845 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Propionitrile | HCID 7854 | — |
| 生成物 | tert-butyl (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylate | HCID 66905345 | 162.4% |
反応手順
A solution of 5-bromo-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (2.0 g, 9.49 mmole), tert-butyl acrylate (1.8 g, 14.1 mmole), Pd(OAc)2 (0.32 g, 1.4 mmole), tri-ortho-tolylphosphine (0.57 g, 1.9 mmole), and diisopropylethylamine (4.9 mL, 28.2 mmole) in propionitrile (100 mL) and DMF (10 mL) was heated at reflux overnight. The dark mixture was filtered through Celite®, and the filtrate was concentrated. Flash chromatography on silica (9:1 CHCl3/CH3OH containing 5% NH4OH) gave the title compound (0.80 g, 33%) as a light yellow solid. MS (ES) m/e 261 (M+H)+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07741339B2 |
| 出典データセット | uspto-grants-2010_06 |
| ORD ID | ord-dc079d50c56847c69bbdaca74f76ae5d |
| 出典メモ | uspto-grants-2010_06 |