HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → HCID 66803515, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 66803653 | HCID 66803653 | — |
| Reactant | 4-Bromo-2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridine | HCID 86280412 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 66803515 | HCID 66803515 | 70% |
Reaction Steps
To a microwave tube was added 4-bromo-2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridine (100 mg, 0.280 mmol), 2-((6-aminopyrimidin-4-yl)methyl)isoindoline-1,3-dione (100 mg, 0.390 mmol), Pd2(dba)3 (32 mg, 0.035 mmol), XantPhos (30 mg, 0.052 mmol), Cs2CO3 (250 mg, 0.770 mmol) in dioxane (5.0 mL). The mixture was degassed with N2 for 10 min. The resulting mixture was irradiated in a microwave reactor at 160° C. for 2 hours and then cooled to room temperature. Insoluble solid was removed via filtration, and the residue was purified with reverse phase column chromatography eluting with a 0-60% gradient of CH3CN in 0.5% NH4HCO3 to give the desired product as a white solid (100 mg, 70% yield). LCMS: m/z: 533.1 [M+H+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08697708B2 |
| Source dataset | uspto-grants-2014_04 |
| ORD ID | ord-b94defb0de44470fa72845fab76259f8 |
| Source note | uspto-grants-2014_04 |