HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tributylphosphine → Methyl 3-cyclopropyl-3-(3-((5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methoxy)phenyl)propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | 1,1'-(Azodicarbonyl)dipiperidine | HCID 73042 | — |
| Reactant | Methyl 3-Cyclopropyl-3-(3-hydroxyphenyl)propanoate | HCID 57706598 | — |
| Reactant | (5-(2-Fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methanol | HCID 117759814 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | Methyl 3-cyclopropyl-3-(3-((5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methoxy)phenyl)propanoate | HCID 117760183 | 65.1% |
Reaction Steps
Under a nitrogen atmosphere, to a solution of (5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methanol (207 mg) and methyl 3-cyclopropyl-3-(3-hydroxyphenyl)propanoate (150 mg) in toluene (9.7 ml) were added 1,1′-(azodicarbonyl)dipiperidine (275 mg) and tributylphosphine (271 μL), and the mixture was stirred at room temperature for 14 hr. Hexane/ethyl acetate (1:1) was added to the reaction mixture, and the resulting precipitate was filtered off. The solvent in the filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (224 mg) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09181186B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-5968c980bbf042a08aecb0629bd13c21 |
| Source note | uspto-grants-2015_11 |