Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Phenylacetylene | HCID 10821 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 178451288 | HCID 178451288 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 178451290 | HCID 178451290 | — |
Reaction Steps
To a mixture of tert-butyl 2-(7-bromo-2-hydroxy-1,1-dimethyl-4-oxo-1,4-dihydronaphthalene-3-carboxamido)acetate (120 mg, 283 μmol, Example 53A-E), palladium dichloride bistriphenylphosphine (20 mg, 28 μmol), and copper(I) iodide (11 mg, 57 μmol) was added THF (1414 μL), N-ethyl-N-isopropylpropan-2-amine (148 μL, 848 μmol), and phenylacetylene (62 μL, 566 μmol). The reaction was heated at 80° C. for 2 hours. The reaction mixture was diluted with 100 mL of EtOAc, washed 2 times with 75 mL of sodium bicarbonate (saturated, aqueous), separated, dried over sodium sulfate, and concentrated to give crude product which was purified via flash chromatography to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07635715B2 |
|---|
| Source dataset | uspto-grants-2009_12 |
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| ORD ID | ord-6df12b79390649439fc4db11ee2f850b |
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| Source note | uspto-grants-2009_12 |
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