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 | Tris(dibenzylideneacetone) dipalladium | HCID 9832798 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67774787 | HCID 67774787 | 76.5% |
Reaction Steps
To an argon purged solution of 2,7-dibromo-[1,2,4]triazolo[1,5-a]pyridine (6.00 g, 21.7 mmol) in dioxane (222 ml) were added tert-butyl carbamate (3.05 g, 26.0 mmol), cesium carbonate (9.88 g, 30.3 mmol), tris(dibenzylideneacetone) dipalladium(0) (397 mg, 433 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (501 mg, 867 μmol). The resulting mixture was heated to 100° C. and stirred for 18 hours under argon atmosphere. The material was applied on silicagel and purified by flash chromatography over a 20 g silicagel column using heptane/ethyl acetate 10-70% as eluent affording (2-bromo-[1,2,4]triazolo[1,5-a]pyridin-7-yl)-carbamic acid tert-butyl ester (5.19 g, 76.5%) as a light yellow solid. MS: m/z=313.0 (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-29fb6237410946da97952206e75f193a |
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| Source note | uspto-grants-2013_01 |
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