Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzylamine | HCID 7504 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 2,6-Dichloro-4-nitropyridine | HCID 3841070 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 15565813 | HCID 15565813 | — |
Reaction Steps
To a solution of 2,6-dichloro-4-nitropyridine (0.1 g, 0.518 mmol) and benzyl amine (0.062 mL, 0.570 mmol) in 10 mL toluene was added cesium carbonate (0.253 g, 0.777 mmol). The mixture was degassed with nitrogen and 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (0.016 g, 0.026 mmol) and palladium acetate (5.82 mg, 0.026 mmol) were added. The mixture was heated at 100° C. for 2 hours, filtered through diatomaceous earth and concentrated. The residue was dissolved in ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, and concentrated. Recrystallization from 1:10 ethyl acetate-hexane afforded the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09073922B2 |
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| Source dataset | uspto-grants-2015_07 |
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| ORD ID | ord-651c70036fbe4cd7ac846c61ab2b17cc |
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| Source note | uspto-grants-2015_07 |
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