Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Allyl Alcohol | HCID 7858 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 2-Bromo-3-pyridinol | HCID 23070 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | Pyridine, 2-bromo-3-(2-propenyloxy)- | HCID 23028574 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Sodium Bicarbonate | HCID 516892 | — |
| Product | HCID 14199079 | HCID 14199079 | — |
Reaction Steps
3-(allyloxy)-2-bromopyridine. Diethyl azodicarboxylate (1 eq.) is added dropwise to a stirring mixture of 2-bromo-3-hydroxypyridine (0.92 eq,), allyl alcohol (0.92 eq), and PPh3 (1.1 eq) in THF (0.2 M) at 0° C. under a N2 atmosphere. The reaction mixture is warmed to 50° C. in an oil bath. Reaction progress is monitored by TLC until judged complete. The reaction mixture is cooled to ambient temperature and diluted with saturated NaHCO3 solution. The aqueous solution is extracted with EtOAc, and the organic layer is dried over Na2SO4 and concentrated. The product that may be thus obtained is purified by column chromatography to afford the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08952009B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-3ab00b8297804d19afbc1f032ca3aa75 |
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| Source note | uspto-grants-2015_02 |
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