Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Iodide | HCID 5238 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-(1H-pyrazol-4-yl)quinoxaline | HCID 4620688 | — |
| Reactant | (R)-ethyl 4-bromo-2-methyl-2-(methylsulfonyl)butanoate | HCID 86670635 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 86710244 | HCID 86710244 | 14% |
Reaction Steps
To a solution of 2-(1H-pyrazol-4-yl)quinoxaline (0.400 g, 1.39 mmol) in acetonitrile (10 mL) was added cesium carbonate (8.73 g, 2.68 mmol, 2.5 eq), sodium iodide (0.032 g, 0.214 mmol, 0.2 eq) and (R)-ethyl 4-bromo-2-methyl-2-(methylsulfonyl)butanoate (0.400 g 1.39 mmol, 1.3 eq). The reaction mixture was heated at 50° C. overnight. The reaction was filtered over a pad of diatomateous earth. The filtrate was evaporated and the crude was purified by flash chromatography on silica gel eluting with 40-100% ethyl acetate/heptane to give ethyl (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(quinoxalin-2-yl)-1H-pyrazol-1-yl]butanoate (0.078 g, 14% yield) as a colorless oil. LC-MS M+H+403.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08809333B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-8537ca90a6124d2e92100fad05960d26 |
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| Source note | uspto-grants-2014_08 |
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