Ethyl Acetate → HCID 50993867, Verbindung

HRID 1784831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1784831
CC1(C)C(C)(C)OB([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][N:13]3[Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])O1.[Br:29][C:30]1[CH:35]=[C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)[CH:33]=[C:32](I)[CH:31]=1.C(=O)([O-])[O-].[Na+].[Na+].CCOC(C)=O>C(O)C.C1(C)C=CC=CC=1.O.[Cl-].[Na+].O>[Br:29][C:30]1[CH:31]=[C:32]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][N:13]3[Si:18]([CH:25]([CH3:26])[CH3:27])([CH:22]([CH3:23])[CH3:24])[CH:19]([CH3:21])[CH3:20])[CH:33]=[C:34]([O:36][CH2:37][C:38]2[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=2)[CH:35]=1

Komponenten

9

Edukt 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 27955744-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-(triisopropylsilyl)-1H-indoleHCID 509940261-Bromo-3-iodo-5-(4-methoxy-benzyloxy)-benzene

Produkt 1

HCID 50993867HCID 50993867, VerbindungAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A 1 L flask was charged with 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-indole (17.44 g, 43.67 mmol) and 1-Bromo-3-iodo-5-(4-methoxy-benzyloxy)-benzene (18.30 g, 43.67 mmol) in ethanol (180 mL) and toluene (180 mL) under argon. Tetrakis-triphenylphosphin-palladium (1.51 g, 1.31 mmol) was added. Then a solution of sodium carbonate (9.26 g, 87.34 mmol) in water (92.6 mL) was added and the mixture heated to 90° C. and stirred for 14 h. After cooling down to room temperature AcOEt (300 mL) and brine (200 mL) were added under stirring. The mixture was filtered through a pad of Hyflo. After separation of the layers the aqueous one was extracted with AcOEt (2×300 mL). The combined organic layers were washed with water and brine (150 mL), dried over Na2SO4, filtered and evaporated to dryness. After flash chromatography on silica gel (1 kg, AcOEt/heptane 1:19) 4-[3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-1-triisopropylsilanyl-1H-indole (22.5 g, 91%) was obtained as a colorless oil.

Aufarbeitung

  1. additionwere added
  2. stirringunder stirring
  3. filtrationThe mixture was filtered through a pad of Hyflo
  4. customAfter separation of the layers the aqueous one
  5. extractionwas extracted with AcOEt (2×300 mL)
  6. washThe combined organic layers were washed with water and brine (150 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-248392b0c6ba4032a2242aa879019276
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504401B2

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