Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Bromo-5-(methylsulfonyl)pyridine | HCID 9899483 | — |
| Reactant | 4-Nitro-3-(tetrahydro-2H-pyran-4-yloxy)phenol | HCID 66726172 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 66726062 | HCID 66726062 | 81% |
Reaction Steps
A mixture of 4-nitro-3-(tetrahydro-2H-pyran-4-yloxy)phenol (23.0 g), 2-bromo-5-(methylsulfonyl)pyridine (22.7 g), cesium carbonate (62.6 g), and N,N-dimethylformamide (200 mL) was stirred at 100° C. for 1.5 hr. The reaction solution was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate-tetrahydrofuran. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The obtained solid was washed with diethyl ether-hexane to give the title compound (30.0 g, yield 81%) as a brown solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08557805B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-0ade291b26a749809124f38441ba821f |
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| Source note | uspto-grants-2013_10 |
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