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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1026595Generated: October 31, 2026

Toluene → HCID 68006358, compound

https://huagongshe.com/reaction/1026595

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantCesium carbonateHCID 10796—
Reactant3,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 74265—
ReactantHCID 68006368HCID 68006368—
CatalystCopper iodideHCID 83717—
SolventMethanolHCID 887—
SolventWaterHCID 962—
ProductHCID 68006358HCID 6800635824.9%

Reaction Conditions

Temperature80 °C

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08729095B2
Source datasetuspto-grants-2014_05
ORD IDord-baffaebab35d4915ac73cd5436e77a75
Source noteuspto-grants-2014_05