Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | HCID 22627650 | HCID 22627650 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22627647 | HCID 22627647 | 101.1% |
Reaction Steps
Under nitrogen atmosphere, 1.2 g of 2-cyano-7-methoxy-8-trifluoromethanesulfonyloxynaphthalene, 0.66 g of phenylboronic acid, 0.12 g of tetrakis triphenylphosphine palladium and 1.5 ml of triethyl- amine were suspended in 20 ml of anhydrous N, N-dimethylformamide. The resulting suspension was stirred under heating at 100° C. for 1.5 hours and cooled to room temperature by allowing to stand. A saturated aqueous solution of ammonium chloride was added to the resulting reaction mixture, followed by the extraction with ethyl acetate (50 ml×2). The organic layers were combined, washed with brine, died over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the resulting crude product was purified by silica gel column chromatography to give 0.95 g of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06358995B1 |
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| Source dataset | uspto-grants-2002_03 |
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| ORD ID | ord-9838e43dfc604371892807902b667839 |
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| Source note | uspto-grants-2002_03 |
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