Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Quinoline, 3-bromo-8-nitro- | HCID 79286 | — |
| Reactant | 1,4-Diazabicyclo(3.2.2)nonane | HCID 398407 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | Binap, (A+-)- | HCID 634876 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 9814764 | HCID 9814764 | 71.9% |
Reaction Steps
1.54 g (6.1 mmol) of 3-bromo-8-nitro_quinoline, 0.7 g (5.5 mmol) of 1,4-diazabicyclo—[3.2.2]nonane, 0.05 g (0.22 mmol) of palladium diacetate, 2.5 g (7.7 mmol) of cesium carbonate and 0.137 g (0.22 mmol) of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, in 30 ml of tetrahydrofuran and 10 ml of toluene, are introduced consecutively into a 100 ml three-necked round-bottomed flask and the reaction mixture is heated at 80-90° C. for 24 h. The inorganic products are separated by filtration and the solvent is evaporated under reduced pressure. The residue is purified by chromatography on a silica gel column, with the elution being carried out using a 95/5/0.5, and then a 90/10/1, mixture of dichloromethane, methanol and ammonia. 1.18 g of solid are obtained, with this solid then being recrystallized in methanol.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06835730B2 |
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| Source dataset | uspto-grants-2004_12 |
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| ORD ID | ord-9affa0c960874479a572c044febdb7e1 |
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| Source note | uspto-grants-2004_12 |
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