Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Chloropyrazine | HCID 73277 | — |
| Reactant | HCID 58292699 | HCID 58292699 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58292770 | HCID 58292770 | 81.2% |
Reaction Steps
A mixture of ethyl 2-(1,6-dihydroxy-4-methoxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (0.15 g, 0.56 mmol), cesium carbonate (0.37 g, 1.12 mmol) and 2-chloropyrazine (96 mg, 0.84 mmol) in DMF (2 mL) was heated to 90° C. for 3 hr. The reaction mixture was quenched by saturated aqueous NaHCO3 (20 mL) and extracted with EtOAc (15 mL×2). The combined extracts were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (EtOAc/PE=1/2) on silica gel to give the title compound as a light yellow solid (156 mg, Y: 81.2%). MS (ESI) m/z=345 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08343944B2 |
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| Source dataset | uspto-grants-2013_01 |
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| ORD ID | ord-bb8415805f6e4141aafaf120984fa354 |
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| Source note | uspto-grants-2013_01 |
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