Potassium Phosphate, Tribasic → (4'-{1-ethyl-1-[3-methyl-4-((E)-4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butenyl)-phenyl]-propyl}-2'-methyl-biphenyl-3-yl)acetic acid methyl ester

HRID 546934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 546934
C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:38]([C:40]([C:59]1[CH:64]=[CH:63][C:62](/[CH:65]=[CH:66]/[C:67]([C:73]([F:76])([F:75])[F:74])([OH:72])[C:68]([F:71])([F:70])[F:69])=[C:61]([CH3:77])[CH:60]=1)([C:43]1[CH:48]=[CH:47][C:46](B2OC(C)(C)C(C)(C)O2)=[C:45]([CH3:58])[CH:44]=1)[CH2:41][CH3:42])[CH3:39].[CH3:78][O:79][C:80](=[O:89])[CH2:81][C:82]1[CH:87]=[CH:86][CH:85]=[C:84](Br)[CH:83]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:78][O:79][C:80](=[O:89])[CH2:81][C:82]1[CH:83]=[C:84]([C:46]2[CH:47]=[CH:48][C:43]([C:40]([CH2:41][CH3:42])([C:59]3[CH:64]=[CH:63][C:62](/[CH:65]=[CH:66]/[C:67]([OH:72])([C:73]([F:75])([F:76])[F:74])[C:68]([F:71])([F:70])[F:69])=[C:61]([CH3:77])[CH:60]=3)[CH2:38][CH3:39])=[CH:44][C:45]=2[CH3:58])[CH:85]=[CH:86][CH:87]=1

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 11746402Methyl 2-(3-bromophenyl)acetateHCID 57708964(E)-4-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1,1,1-trifluoro-2-trifluoromethyl-3-buten-2-ol

Produkt 1

HCID 57709177(4'-{1-ethyl-1-[3-methyl-4-((E)-4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butenyl)-phenyl]-propyl}-2'-methyl-biphenyl-3-yl)acetic acid methyl esterAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Palladium acetate (3.6 mg, 0.016 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (13.1 mg, 0.032 mmol), potassium phosphate (51 mg, 0.24 mmol) and water (0.04 mL) were added to a solution of (E)-4-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1,1,1-trifluoro-2-trifluoromethyl-3-buten-2-ol (Example 26-(5); 40 mg, 0.070 mmol) and (3-bromo-phenyl)acetic acid methyl ester (Tetrahedron Letters 44 (2003) 331-334; 28 mg, 0.122 mmol) in toluene (0.4 mL). After replacement with nitrogen, the mixture was stirred at 100° C. for 30 minutes. Then, the reaction mixture was concentrated under reduced pressure, and the residue was dissolved in dichloromethane. Thereafter, the solution was filtered through amino silica gel, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1) to give the target compound as a colorless oil (12.8 mg, 31%).

Aufarbeitung

  1. concentrationThen, the reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. filtrationThereafter, the solution was filtered through amino silica gel
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-ae6a49e8a49a48de8e638898fd4c556d
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935688B2

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