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 | 8-Bromo-6-chloroimidazo(1,2-a)pyridine | HCID 26370038 | — |
| Reactant | 5-[4-(3-Oxetanyl)-1-piperazinyl]-2-pyridinamine | HCID 86684125 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86684122 | HCID 86684122 | 66.1% |
Reaction Steps
A 50-mL round-bottomed flask equipped with a reflux condenser was charged with 8-bromo-6-chloroimidazo[1,2-a]pyridine 101a (264 mg, 1.14 mmol), 5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-amine (328 mg, 1.14 mmol), Pd2(dba)3 (102 mg, 0.11 mmol), Xantphos (63 mg, 0.11 mmol), Cs2CO3 (3.58 g, 11.0 mmol), dioxane (20 mL). After three cycles of vacuum/argon flush, the mixture was heated at 100° C. overnight. It was then filtered and the filtrate was evaporated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 1:50 methanol/dichloromethane to afford 121a as an orange solid (290 mg, 66%). MS-ESI: [M+H]+ 385.1
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-5dd6aec2a3f647f5ac672080463fc441 |
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| Source note | uspto-grants-2014_05 |
|---|
