Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-Fluoro-4-methoxyphenylboronic acid | HCID 2782194 | — |
| Reactant | Ethyl 5,6-Dichloronicotinate | HCID 16762519 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67513659 | HCID 67513659 | — |
Reaction Steps
Ethyl 5,6-dichloronicotinate (1 g, 4.54 mmol), 3-fluoro-4-methoxyphenylboronic acid (0.965 g, 5.68 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.371 g, 0.454 mmol), cesium carbonate (3.26 g, 10.00 mmol) and THF (30 mL) were refluxed in an 80° C. oil bath under N2 for 2.5 hrs. Volatiles were removed under reduced pressure. The pot residue was worked up with brine, extracted with ethyl acetate, dried over Na2SO4, filtered and evaporated to afford a dark mixture. The resulting crude mixture was purified by flash chromatography (SiO2, Biotage 65i cartridge). The column was eluted by an EtOAc/hexanes mixture (0% to 40%). Related fractions were pooled and evaporated to afford a white fluffy solid as the titled compound. LCMS calc.=309.06. found=310.01 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09221834B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-52480f1b07e84569a3c78163b5140062 |
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| Source note | uspto-grants-2015_12 |
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