Potassium Phosphate, Tribasic → HCID 57709095, Verbindung

HRID 546899Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 546899
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][CH:6]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH2:50]([C:52]([C:74]1[CH:79]=[CH:78][C:77](B2OC(C)(C)C(C)(C)O2)=[C:76]([CH3:89])[CH:75]=1)([C:55]1[CH:60]=[CH:59][C:58]([C:61]#[C:62][C:63]2([O:68][Si:69]([CH3:72])([CH3:71])[CH3:70])[CH2:67][CH2:66][CH2:65][CH2:64]2)=[C:57]([CH3:73])[CH:56]=1)[CH2:53][CH3:54])[CH3:51].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:77]2[CH:78]=[CH:79][C:74]([C:52]([CH2:53][CH3:54])([C:55]3[CH:60]=[CH:59][C:58]([C:61]#[C:62][C:63]4([O:68][Si:69]([CH3:71])([CH3:72])[CH3:70])[CH2:67][CH2:66][CH2:65][CH2:64]4)=[C:57]([CH3:73])[CH:56]=3)[CH2:50][CH3:51])=[CH:75][C:76]=2[CH3:89])=[CH:7][CH:6]=1

Komponenten

9

Edukt 5

HCID 62657Potassium Phosphate, TribasicHCID 316783Methyl 2-(4-bromophenyl)acetateHCID 516892Sodium BicarbonateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 577089762-(4-{1-Ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclopentylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Produkt 1

HCID 57709095HCID 57709095, VerbindungAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

(4-Bromo-phenyl)acetic acid methyl ester (Tetrahedron Letters 44 (2003) 331-334; 34 mg, 0.147 mmol), palladium acetate (2.2 mg, 0.010 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (8.2 mg, 0.020 mmol), potassium phosphate (62 mg, 0.294 mmol) and water (0.2 mL) were added to a solution of 2-(4-{1-ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclopentylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 32-(4); 54.6 mg, 0.098 mmol) in toluene (2 mL). After replacement with nitrogen, the mixture was stirred at 100° C. for 2.5 hours. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1) to give the target compound as a colorless oil (36.5 mg, 64%).

Aufarbeitung

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-d7998ed0149b451fb40005cb5d24a496
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935688B2

Notizen zur Reaktion

Wird geladen…