HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-Butyl acrylate → tert-butyl (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-Butyl acrylate | HCID 15458 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 5-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one | HCID 15504062 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Propionitrile | HCID 7854 | — |
| Product | tert-butyl (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylate | HCID 66905345 | 162.4% |
Reaction Steps
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)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08153652B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-4dc6f2dcbf814ee5a42ed537b70e83be |
| Source note | uspto-grants-2012_04 |