HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → (9S)-9-[4-(4-ethylphenoxy)phenyl]-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Boronic acid, (4-ethylphenyl)- | HCID 2734352 | — |
| Reactant | 4-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenol | HCID 66748496 | — |
| Catalyst | HCID 178476681 | HCID 178476681 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (9S)-9-[4-(4-ethylphenoxy)phenyl]-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide | HCID 66748080 | 19.2% |
Reaction Steps
A mixture of (4-ethylphenyl)boronic acid (802 mg), 4-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenol (500 mg), pyridine (3.60 mL), cesium carbonate (581 mg), diacetoxycopper (648 mg), and powdered 4A MS (5.00 g) in MeCN (18 ml) was stirred at room temperature overnight. The mixture was added with NH silica gel, concentrated in vacuo, and purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) then recrystallized from EtOAc to give the title compound (132 mg) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08575154B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-3387951346f047eab972f893f097d743 |
| Source note | uspto-grants-2013_11 |