Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | tert-Butyl carbamate | HCID 77922 | — |
| Reactant | 2,7-Dibromo[1,2,4]triazolo[1,5-a]pyridine | HCID 67774274 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67774787 | HCID 67774787 | 64.7% |
Reaction Steps
To an argon purged solution of 2,7-dibromo-[1,2,4]triazolo[1,5-a]pyridine (1.9 g, 6.86 mmol) in dioxane (70.3 ml) are added tert-butyl carbamate (965 mg, 8.23 mmol), cesium carbonate (3.13 g, 9.61 mmol), tris(dibenzylideneacetone)dipalladium(0) (126 mg, 137 μmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (159 mg, 274 μmol). The resulting mixture is stirred for 18 hours at 100° C. under argon atmosphere. The crude material is loaded on silicagel and purified by chromatography on a 70 g silica column using heptane/ethyl acetate 10-40% as eluent affording tert-butyl 2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamate (1.39 g, 64.6%) as a white solid. MS: m/z=313.0; 314.9 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08349824B2 |
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| Source dataset | uspto-grants-2013_01 |
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| ORD ID | ord-fe20415eda154b6eb64d1f9d361fde28 |
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| Source note | uspto-grants-2013_01 |
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