HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → HCID 66644374, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| Reactant | Methyl 5-hydroxypyridine-2-carboxylate | HCID 4715126 | — |
| Reactant | [3-(5-Fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-methanol | HCID 66599256 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66644374 | HCID 66644374 | 108.7% |
Reaction Steps
To a solution of [3-(5-fluoro-pyridin-2-yl)-5-methyl-isoxazol-4-yl]-methanol (854 mg, 4.1 mmol) in THF (40 mL) was added 5-hydroxy-pyridine-2-carboxylic acid methyl ester (691 mg, 4.5 mmol) and triphenylphosphine (1.61 g, 6.1 mmol) at ambient temperature under an argon atmosphere. Then diethyl azodicarboxylate (2.82 mL, 40% solution in toluene, 6.0 mmol) was added and the reaction mixture was stirred for 2 h at room temperature. The reaction mixture was evaporated and then purified by chromatography (silica, heptane:ethyl acetate=100:0 to 2:3) to afford the title compound (1.53 g, 76%) as an off white solid. MS: m/e=344.0 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08415379B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-5901c3e98436476ea69edd6fb0bec122 |
| Source note | uspto-grants-2013_04 |