HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 2-(5-Chloro-2-fluoro-phenyl)-4-isoquinolin-4-yl-[1,8]naphthyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | Isoquinoline-4-boronic acid | HCID 3761204 | — |
| Reactant | 4-Chloro-2-(5-chloro-2-fluoro-phenyl)-[1,8]naphthyridine | HCID 53344724 | — |
| Solvent | Water | HCID 962 | — |
| Product | 2-(5-Chloro-2-fluoro-phenyl)-4-isoquinolin-4-yl-[1,8]naphthyridine | HCID 66631753 | 77.8% |
Reaction Steps
426 mg 4-chloro naphthyridine from example 1, 682 mg 4-isoquinoline boronic acid pinacole ester, 945 mg sodium carbonate were dissolved with 30 ml dioxan and 3 ml water, flushed with nitrogen, and 172 mg tetrakistriphenylphosphine palladium(0) were added. After 105 min reflux workup as in example 20 yielded a brownish oil, which was crystallized with ether to give 436 mg of product with correct LC-MS: M+H+ 386 and Rt˜2.22 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08912216B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-2431ab0be9644dd088df07261bc136d6 |
| Source note | uspto-grants-2014_12 |