Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 22329280 | HCID 22329280 | — |
| Reactant | 4-Morpholinophenyl borate | HCID 86756179 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 22328989 | HCID 22328989 | 83.2% |
Reaction Steps
A mixture of methyl 7-bromo-1-methoxycarbonyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.3 g), 4-morpholinophenyl borate (0.22 g), 1M potassium carbonate solution (2.5 ml), ethanol (2.5 ml) and toluene (25 ml) was stirred under argon atmosphere at room temperature for 30 minutes. To the mixture was added tetrakis(triphenylphosphine)palladium (0.04 g), and the mixture was refluxed overnight under argon atmosphere and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried with anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate/hexane) to give methyl 1-methoxycarbonyl-7-(4-morpholinophenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (0.31 g) as pale yellow crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06936602B1 |
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| Source dataset | uspto-grants-2005_08 |
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| ORD ID | ord-4e4090133f684457999e6023290fa6bc |
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| Source note | uspto-grants-2005_08 |
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