HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tributylphosphine → Ethyl 3-(2-(((2-(2-cyano-2-methylpropyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)oxy)methyl)pyridin-4-yl)-3-cyclopropylpropanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tributylphosphine | HCID 13831 | — |
| Reactant | 1,1'-(Azodicarbonyl)dipiperidine | HCID 73042 | — |
| Reactant | Ethyl 3-cyclopropyl-3-(2-(hydroxymethyl)pyridin-4-yl)propanoate | HCID 117759601 | — |
| Reactant | 3-(2'-Fluoro-4-hydroxy-5'-methoxybiphenyl-2-yl)-2,2-dimethylpropanenitrile | HCID 117760136 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | Ethyl 3-(2-(((2-(2-cyano-2-methylpropyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)oxy)methyl)pyridin-4-yl)-3-cyclopropylpropanoate | HCID 117759958 | 87.4% |
Reaction Steps
To a solution of 3-(2′-fluoro-4-hydroxy-5′-methoxybiphenyl-2-yl)-2,2-dimethylpropanenitrile (151 mg), ethyl 3-cyclopropyl-3-(2-(hydroxymethyl)pyridin-4-yl)propanoate (168 mg) and tributylphosphine (0.25 mL) in toluene (5.0 mL) was added 1,1′-(azodicarbonyl)dipiperidine (256 mg), and the mixture was stirred at room temperature for 3 hr. Hexane was added to the reaction mixture, and the mixture was filtered through celite. 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 (234 mg) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09382188B2 |
| Source dataset | uspto-grants-2016_07 |
| ORD ID | ord-172ebd4c76044e6793c85ec24d6d4f83 |
| Source note | uspto-grants-2016_07 |