Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
tert-Butyl acrylate → tert-butyl (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylate
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | tert-Butyl acrylate | HCID 15458 | — |
| 반응물 | Tri-o-tolylphosphine | HCID 80271 | — |
| 반응물 | Diisopropylethylamine | HCID 81531 | — |
| 반응물 | 5-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one | HCID 15504062 | — |
| 촉매 | palladium(II) acetate | HCID 167845 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 용매 | Propionitrile | HCID 7854 | — |
| 생성물 | tert-butyl (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylate | HCID 66905345 | 162.4% |
반응 단계
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)+.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US07879872B2 |
| 출처 데이터셋 | uspto-grants-2011_02 |
| ORD ID | ord-e0583c40d6b0427e853d1cb4a0714470 |
| 출처 메모 | uspto-grants-2011_02 |