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 | tert-Butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate | HCID 11737525 | — |
| Reactant | 8-Bromo-6-chloroimidazo(1,2-a)pyridine | HCID 26370038 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86684120 | HCID 86684120 | 78% |
Reaction Steps
A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and reflux condenser was charged with 1,4-dioxane (60 mL), tert-butyl 4-(6-aminopyridin-3-yl)piperazine-1-carboxylate (1.5 g, 5.39 mmol), 8-bromo-6-chloroimidazo[1,2-a]pyridine 101a (3.7 g, 16.18 mmol), and cesium carbonate (3.52 g, 10.79 mmol). XantPhos (312 mg, 0.539 mmol) and Pd2(dba)3 (494 mg, 0.539 mmol) were added, and the reaction mixture was heated at 100° C. for 5 h under nitrogen. After this time the reaction was cooled to room temperature. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified on flash column eluting with 100:1 CH2Cl2/MeOH to afford 102a (1.8 g, 78%). MS: [M+H]+ 429.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08722676B2 |
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| Source dataset | uspto-grants-2014_05 |
|---|
| ORD ID | ord-17376b86b8bc4f828a72a5b39ac79078 |
|---|
| Source note | uspto-grants-2014_05 |
|---|
