HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Oxygen → 1-[(3'-Chloro-2',6'-difluoro-6,4'-dimethoxy-biphenyl-3-carbonyl)-amino]-4-methyl-cyclohexanecarboxylic Acid Methyl Ester
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Oxygen | HCID 977 | — |
| Edukt | Potassium Fluoride | HCID 522689 | — |
| Edukt | Tri-tert-butylphosphine tetrafluoroborate | HCID 2734635 | — |
| Edukt | 1-(3-Bromo-4-methoxy-benzoylamino)-4-methyl-cyclohexanecarboxylic acid methyl ester | HCID 67171124 | — |
| Edukt | 3-Chloro-2,6-difluoro-4-methoxyphenylboronic Acid | HCID 86672570 | — |
| Katalysator | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Lösungsmittel | 1,4-Dioxane | HCID 31275 | — |
| Produkt | 1-[(3'-Chloro-2',6'-difluoro-6,4'-dimethoxy-biphenyl-3-carbonyl)-amino]-4-methyl-cyclohexanecarboxylic Acid Methyl Ester | HCID 86672571 | 39,9% |
Reaktionsschritte
300 mg of 1-(3-Bromo-4-methoxy-benzoylamino)-4-methyl-cyclohexanecarboxylic acid methyl ester, 36 mg of tris(dibenzylideneacetone)di-palladium(0), 150 mg of KF, 27 mg of tri-tert-butylphosphonium tetrafluoroborate, and 347 mg of 3-Chloro-2,6-difluoro-4-methoxyphenylboronic acid were suspended using 5 ml of anhydrous dioxane and oxygen was removed by passing argon through. Then, 12 mg of N,N-diisopropylethylamine were added and again argon passed through the suspension. Stirring was continued for 24 h at room temperature. The reaction mixture was then filtered and evaporated. The residue was purified by preparative RP HPLC (water/ACN gradient) to yield 150 mg of the title compound, viscous oil.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09018383B2 |
| Quelldatensatz | uspto-grants-2015_04 |
| ORD ID | ord-a6cfdf19f7614c398074289cf0de505f |
| Quellennotiz | uspto-grants-2015_04 |