Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | (4-Bromophenyl)boronic acid | HCID 79599 | — |
| Reactant | Calcium Chloride | HCID 5284359 | — |
| 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 | Pyridine | HCID 1049 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 66748590 | HCID 66748590 | 6.5% |
Reaction Steps
Diacetoxycopper (648 mg) was added to a mixture of pyridine (0.433 mL), (4-bromophenyl)boronic acid (1075 mg), cesium carbonate (581 mg) and 4-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenol (500 mg) in MeCN (35 mL). The mixture was stirred at room temperature under a dry atmosphere (anhydrous calcium chloride tube) for 19 hr. The insoluble, light-blue precipitates were removed by filtration through Celite-pad (eluted with EtOAc). Silica-gel was added to the filtrate and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) and concentrated in vacuo. The residue was crystallized from THF/IPE to give the title compound (50.6 mg) as colorless crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08778934B2 |
|---|
| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-a04619badf464fdb9d07dee2ceddc863 |
|---|
| Source note | uspto-grants-2014_07 |
|---|