Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3,4,7,8-Tetramethyl-1,10-phenanthroline | HCID 74265 | — |
| Reactant | HCID 68006368 | HCID 68006368 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 68006358 | HCID 68006358 | 24.9% |
Reaction Steps
To a toluene suspension (5.6 ml) of tert-butyl 4-(7-bromo-3,3-dimethyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)piperidine-1-carboxylate (Example 52-1) (1.11 g), copper iodide (24.0 mg), 3,4,7,8-tetramethyl-1,10-phenanthroline (59.6 mg) and cesium carbonate (1.23 g) was added methanol (0.204 ml), followed by stirring at 80° C. for 21 hours. After the reaction solution was brought back to room temperature, water was added, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford tert-butyl 4-(7-methoxy-3,3-dimethyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-1-yl)piperidine-1-carboxylate (246 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08729095B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-baffaebab35d4915ac73cd5436e77a75 |
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| Source note | uspto-grants-2014_05 |
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