HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Amino-5-bromopyridine → benzyl (E)-3-(6-aminopyridin-3-yl)acrylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Amino-5-bromopyridine | HCID 70622 | — |
| Reactant | Benzyl acrylate | HCID 75617 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Propionitrile | HCID 7854 | — |
| Product | benzyl (E)-3-(6-aminopyridin-3-yl)acrylate | HCID 11128853 | 39.3% |
Reaction Steps
A solution of 2-amino-5-bromopyridine (2.25 g, 13.0 mmole), benzyl acrylate (3.2 g, 19.7 mmole), Pd(OAc)2 (0.31 g, 1.4 mmole), tri-ortho-tolylphosphine (0.73 g, 2.4 mmole), and diisopropylethylamine (3.5 mL, 20.0 mmole) in propionitrile (50 mL) was heated at reflux overnight. The dark mixture was filtered through Celite®, and the filtrate was concentrated. Flash chromatography on silica gel (3% MeOH/CH2Cl2) gave the title compound (1.3 g, 39%): MS (ES) m/e 255 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07741339B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-084ea8b076b0498e837cf0a5106a25e5 |
| Source note | uspto-grants-2010_06 |