HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tributylphosphine → Methyl 3-cyclopropyl-3-(3-((5-(2-fluoro-5-methoxyphenyl)-6-isobutoxypyridin-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-isobutoxypyridin-2-yl)methanol | HCID 117760235 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | Methyl 3-cyclopropyl-3-(3-((5-(2-fluoro-5-methoxyphenyl)-6-isobutoxypyridin-2-yl)methoxy)phenyl)propanoate | HCID 117760024 | 79% |
Reaction Steps
Under a nitrogen atmosphere, to a solution of (5-(2-fluoro-5-methoxyphenyl)-6-isobutoxypyridin-2-yl)methanol (100 mg) and methyl 3-cyclopropyl-3-(3-hydroxyphenyl)propanoate (72 mg) in toluene (4.7 mL) were added 1,1′-(azodicarbonyl)dipiperidine (132 mg) and tributylphosphine (131 μL), and the mixture was stirred at room temperature for 14 hr. To the reaction mixture was added hexane/ethyl acetate (1:1), and the resulting precipitate was removed by filtration. 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 (131 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-0c3714d49f2a46ce8a9f8d6047eb9e4e |
| Source note | uspto-grants-2015_11 |