HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Benzenamine, 3,5-bis(trifluoromethyl)- → 2-[5-(3,5-Bis-trifluoromethyl-phenylamino)-4'-chloro-3'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid methyl ester
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Benzenamine, 3,5-bis(trifluoromethyl)- | HCID 9480 | — |
| Edukt | (1,1'-Binaphthalen)-2-yldi-tert-butylphosphine | HCID 2734941 | — |
| Edukt | Sodium t-butoxide | HCID 23676156 | — |
| Edukt | 2-(4'-Chloro-5-trifluoromethanesulfonyloxy-3'-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid methyl ester | HCID 57754964 | — |
| Katalysator | palladium(II) acetate | HCID 167845 | — |
| Lösungsmittel | Toluene | HCID 1140 | — |
| Produkt | 2-[5-(3,5-Bis-trifluoromethyl-phenylamino)-4'-chloro-3'-trifluoromethyl-biphenyl-3-yl]-4-methyl-pentanoic acid methyl ester | HCID 57755056 | 45,8% |
Reaktionsschritte
A mixture of 2-(4′-chloro-5-trifluoromethanesulfonyloxy-3′-trifluoromethyl-biphenyl-3-yl)-4-methyl-pentanoic acid methyl ester (48 mg, 0.10 mmol), 3,5-bis-(trifluoromethyl)-aniline (18 μL, 0.12 mmol), sodium tert-butoxide (9.8 mg, 0.10 mmol), Pd(OAc)2 (2.5 mg, 0.01 mmol), 2-(di-tert-butylphoshino-1,1′-binaphthyl (3.5 mg, 0.01 mmol) and toluene (1 mL) was stirred under microwave irradiation at 130° C. for 3×10 min. The mixture was diluted with toluene (9 mL), washed with 1M HCl (2×10 mL) and brine (10 mL), dried (MgSO4), concentrated in vacuo and purified by flash column chromatography (diethylether-petroleum ether) to afford the title product as a colourless powder (28 mg, 44%). Mass spectrum (ESI, m/z): 610, 612 (M−H).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US07557244B2 |
| Quelldatensatz | uspto-grants-2009_07 |
| ORD ID | ord-f17439eb2c694957a946408cc6238aa7 |
| Quellennotiz | uspto-grants-2009_07 |