HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acrylate → Ethyl (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acrylate | HCID 8821 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 6-Bromo-3,4-dihydro-1,8-naphthyridin-2(1H)-one | HCID 11096325 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Propionitrile | HCID 7854 | — |
| Product | Ethyl (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylate | HCID 66905192 | 59% |
Reaction Steps
A solution of 6-bromo-3,4-dihydro-1H-1,8-naphthyridin-2-one (5.0 g, 21.9 mmole), from Preparation 4, ethyl acrylate (3.3 g, 32.9 mmole), Pd(OAc)2 (1.1 g, 0.74 mmole), tri-ortho-tolylphosphine (1.3 g, 4.4 mmole), and diisopropylethylamine (11.4 mL, 65.7 mmole) in propionitrile (200 mL) and DMF (25 mL) was heated at reflux overnight. The dark mixture was filtered through Celite®, and the filtrate was concentrated. Flash chromatography on silica gel (9:1 CHCl3/CH3OH containing 5% NH4OH) gave the title compound (3.0 g, 59%) as a light yellow solid: MS (ES) m/e 233 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07741339B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-e848bcc541084c97af96ce82d283157e |
| Source note | uspto-grants-2010_06 |