Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 2-Fluorophenol | HCID 9707 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Methyl 5-chloropyrazine-2-carboxylate | HCID 406081 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 71238257 | HCID 71238257 | — |
Reaction Steps
2-Fluorophenol (21.6 g, 233 mmol) was dissolved in DMF (250 mL) under a calcium chloride drying tube. The solution was cooled to 0° C., and then 60% NaH in paraffin oil (9.3 g, 233 mmol) was added in small portions. After the main portion of NaH had dissolved, 5-chloro-pyrazine-2-carboxylic acid methyl ester (Preparation 41, 40.2 g, 233 mmol) was added. The mixture was refluxed for 1 hour and then poured into water (1 L). The aqueous mixture was extracted with ether (3×300 mL), and the combined organic layers were washed with 2% sodium hydroxide aqueous solution (400 mL) and filtered through a layer of silica gel (40/60 prn). The filtrate was concentrated in vacuo to yield the title compound which was used without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08895544B2 |
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| Source dataset | uspto-grants-2014_11 |
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| ORD ID | ord-1d240826ff46495d8b47974c5b91930c |
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| Source note | uspto-grants-2014_11 |
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