Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phenol | HCID 996 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Bromo-2-chloro-5-nitropyridine | HCID 230889 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 86721028 | HCID 86721028 | 91% |
Reaction Steps
Phenol (0.416 g, 4.42 mmol), 3-bromo-2-chloro-5-nitropyridine (Combi-Blocks, CAS [5470-17-7], 1 g, 4.21 mmol) and cesium carbonate (1.372 g, 4.21 mmol) were combined in DMSO (8 mL) and heated at 80° C. for 30 minutes. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the residue by chromatography (silica gel, 0-30% ethyl acetate in hexanes) afforded the title compound (1.13 g, 91%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09296741B2 |
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| Source dataset | uspto-grants-2016_03 |
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| ORD ID | ord-d1dbb8891b904f67b76e42a90492a33d |
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| Source note | uspto-grants-2016_03 |
|---|