HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 4-Chloro-5,7-difluoro-3-methyl-2-(5-(methylthio)pyridin-3-yl)quinoline
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | (5-(Methylsulfanyl)pyridin-3-yl)boronic acid | HCID 22392014 | — |
| Reactant | 2,4-Dichloro-5,7-difluoro-3-methylquinoline | HCID 59631040 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water | HCID 962 | — |
| Product | 4-Chloro-5,7-difluoro-3-methyl-2-(5-(methylthio)pyridin-3-yl)quinoline | HCID 59631284 | — |
Reaction Steps
Prepared according to procedure F by stirring 2,4-dichloro-5,7-difluoro-3-methylquinoline (600 mg, 2.419 mmol), 5-(methylthio)pyridin-3-ylboronic acid (429 mg, 2.54 mmol), PdCl2(PPh3)2 (170 mg, 0.242 mmol), sodium carbonate (769 mg, 7.26 mmol), 1,4-dioxane (6.5 mL), and water (1.6 mL) at 95° C. for 2 h. Purification by column chromatography (silica gel, 0-30% EtOAc in hexanes) gave 4-chloro-5,7-difluoro-3-methyl-2-(5-(methylthio)pyridin-3-yl)quinoline. Mass Spectrum (ESI) m/e=337.0 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08765940B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-e0929ba705034964970a58f4af737b70 |
| Source note | uspto-grants-2014_07 |