Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | HCID 86677177 | HCID 86677177 | — |
| Reactant | HCID 131734651 | HCID 131734651 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Product | HCID 89484872 | HCID 89484872 | 7% |
Reaction Steps
To a solution of tert-butyl(2,4-difluorophenyl) carbonate (2.21 g, 9.6 mmol, 1.2 eq.) in THF (150 mL) cooled at −78° C. was added n-BuLi (3.84 mL, 9.6 mmol, 1.2 eq.) dropwise. The resulting mixture was stirred at −78° C. for 30 min, then a solution of 3-chloro-N-methoxy-N-methylquinoxaline-6-carboxamide (2.0 g, 9.6 mmol, 1.0 eq.) in THF (50 mL) was added dropwise. The resulting mixture was stirred at −78° C. for 1 h, then quenched by the addition of NH4Cl solution. The mixture was extracted with EA (100 mL×3). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified via flash column chromatography (PE/EA=4/1, v/v) to afford tert-butyl (3-(3-chloroquinoxaline-6-carbonyl)-2,4-difluorophenyl) carbonate as a yellow oil (240 mg, 7%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09249111B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-8c6952dce4f84b898b319a35d5ea0a8d |
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| Source note | uspto-grants-2016_02 |
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