Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | tert-Butyl carbamate | HCID 77922 | — |
| Reactant | 7-Bromo-2-(4-morpholinyl)[1,2,4]triazolo[1,5-a]pyridine | HCID 67776860 | — |
| 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 67776770 | HCID 67776770 | 101.1% |
Reaction Steps
To an argon purged solution of 4-(7-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)morpholine (321 mg, 1.13 mmol) in dioxane (8 ml) are added tert-butyl carbamate (159 mg, 1.36 mmol), tris(dibenzylideneacetone)dipalladium(0) (20.8 mg, 22.7 μmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (26.2 mg, 45.4 μmol) and cesium carbonate (517 mg, 1.59 mmol). The reaction vessel is sealed and heated to 110° C. for 20 hours. The crude material is applied on silica and purified by flash chromatography on a 20 g silica column using heptane/ethyl acetate 10-70% as eluent affording tert-butyl 2-morpholino-[1,2,4]triazolo[1,5-a]pyridin-7-ylcarbamate (365 mg, 101%) as a light yellow solid. mp.: 92-3° C. MS: m/z=320.1 (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-2393d27c215b47d793a167c03b22b165 |
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| Source note | uspto-grants-2013_01 |
|---|
