Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diethylphosphite | HCID 3780918 | — |
| Reactant | HCID 18374503 | HCID 18374503 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 18398676 | HCID 18398676 | 13% |
| Product | HCID 18398690 | HCID 18398690 | 4% |
Reaction Steps
To a degassed solution of 6,8-dibromo-2-methylquinoline (3.01 g, 10 mmol, prepared according to Song et al. J. Heterocyclic Chem. 1993, 39, 17.), diethylphosphite (1.65 g, 12 mmol) and Et3N (1.21 g, 12 mmol) in toluene (3 mL) was added Pd(OAc)2 (224.5 mg, 1 mmol). The mixture was degassed and Ph3P (1.049 g, 4 mmol) was added. The mixture was heated to 100° C. for 7 h, cooled, diluted with EtOAc (200 mL) and filtered through celite. The filtrate was concentrated in vacuo. The residue was purified by chromatography on silica gel to give 475 mg (13%) of diethyl 6-bromo-2-methyl-8-quinolylphosphonate and 150 mg (4%) of diethyl 8-bromo-2-methyl-6-quinolylphosphonate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06486141B2 |
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| Source dataset | uspto-grants-2002_11 |
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| ORD ID | ord-8b5a5ab77b6449e1a26b9954b91c07ca |
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| Source note | uspto-grants-2002_11 |
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