HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tributylphosphine → Methyl 3-cyclopropyl-3-(3-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-4-methoxyphenyl)propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | 1,1'-(Azodicarbonyl)dipiperidine | HCID 73042 | — |
| Reactant | (5-(2-Fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methanol | HCID 117759814 | — |
| Reactant | Methyl 3-cyclopropyl-3-(3-hydroxy-4-methoxyphenyl)propanoate | HCID 117760009 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Methyl 3-cyclopropyl-3-(3-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-4-methoxyphenyl)propanoate | HCID 117759994 | 53.3% |
Reaction Steps
Under a nitrogen atmosphere, to a solution of methyl 3-cyclopropyl-3-(3-hydroxy-4-methoxyphenyl)propanoate (168 mg) and (6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methanol (202 mg) in toluene (15 mL) were added 1,1′-(azodicarbonyl)dipiperidine (268 mg) and tributylphosphine (262 and the mixture was stirred at room temperature for 15 hr. Hexane and ethyl acetate were added to the reaction mixture, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (190 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-8447ccedba1b450db95678f0f08521ad |
| Source note | uspto-grants-2015_11 |