HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dimethoxyethane → 8-Ethenyl-2-methoxy-1,5-naphthyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dimethoxyethane | HCID 8071 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 6-Methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonate | HCID 11255265 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Product | 8-Ethenyl-2-methoxy-1,5-naphthyridine | HCID 57599573 | 81% |
Reaction Steps
To a solution of 6-(methyloxy)-1,5-naphthyridin-4-yl trifluoromethanesulfonate (from Prep. 5b) (5.0 g, 16.23 mmole) in DME (80 mL) and H2O (40 mL) was added trivinyl boronate (1.96 g, 8.1 mmole), K2CO3 (2.23 g, 16.23 mmole) and Pd(PPh3)4 (0.19 g, 0.16 mmole). After 3 h at 90° C. under N2, the reaction solution was concentrated under vacuum and purified on silica (hexanes, EtOAc, 4:1) to give a yellow oil (2.44 g, 81%): LC-MS (m/z) (ES) 187 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07691850B2 |
| Source dataset | uspto-grants-2010_04 |
| ORD ID | ord-b581ffb8d7744a6690c3dfeef1a6f0bb |
| Source note | uspto-grants-2010_04 |