Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethylamine | HCID 8021 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate | HCID 77231184 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 70665099 | HCID 70665099 | 60.2% |
Reaction Steps
To a solution of methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (150 mg, 0.47 mmol) in DMSO (2 mL) was added diethylamine (173 mg, 2.37 mmol) and DIEA (170 mg, 1.32 mmol). The resulting solution was stirred overnight at 70° C. and then quenched by the addition of water/ice (40 mL), extracted with ethyl acetate (3×20 mL), the organic layers combined and dried over anhydrous magnesium sulfate and concentrated in vacuo to give a residue. Purification via silica gel column chromatography (0.5%-4% ethyl acetate in petroleum ether) afforded methyl 3-(diethylamino)-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a yellow solid (100 mg, 60%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08912188B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-3ebf8e891f48482b89c3e6942db23389 |
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| Source note | uspto-grants-2014_12 |
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