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Ethanol → 2-Octyl-5-[3-fluoro-4-(5-decylpyrimidine-2-yl)phenyl]indan

HRID 1770183
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1770183
[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](B(O)O)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].O([C:29]1[CH:34]=[CH:33][C:32]([C:35]2[N:40]=[CH:39][C:38]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[CH:37][N:36]=2)=[C:31]([F:51])[CH:30]=1)S(C(F)(F)F)(=O)=O.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.O>[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:29]3[CH:34]=[CH:33][C:32]([C:35]4[N:40]=[CH:39][C:38]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[CH:37][N:36]=4)=[C:31]([F:51])[CH:30]=3)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 200950103-Fluoro-4-(5-decylpyrimidine-2-yl)phenyl triflateHCID 220990862-Octylindane-5-boronic acid

Produkt 1

HCID 200950222-Octyl-5-[3-fluoro-4-(5-decylpyrimidine-2-yl)phenyl]indanAusbeute 73,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysator
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

0.40 g (1.46 mM of 2-octylindan-5-boronic acid, 0.60 g (1.30 mM) of 3-fluoro-4-(5-decylpyrimidine-2-yl)phenyl triflate, 1.2 ml of ethanol, 2 ml of toluene, 2 ml of 2M-sodium carbonate aqueous solution and 0.07 g of tetrakis (triphenylphosphine) palladium (O) were mixed and heat-refluxed for 200 minutes under stirring. After the reaction, the reaction mixture, water and toluene were added to followed by filtration under reduced pressure. The toluene layer was washed with a common salt aqueous solution followed by drying with anhydrous sodium sulfate. Then, the sodium sulfate was removed from the mixture and the resultant mixture was evaporated to obtain a residue. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1) and treated with activated carbon, followed by recrystallization from acetone to obtain 0.52 g of 2-octyl-5-[3-fluoro-4-(5-decylpyrimidine-2-yl)phenyl]indan (Yield: 73.8%). ##STR316##

Aufarbeitung

  1. temperatureheat-refluxed for 200 minutes
  2. customAfter the reaction
  3. filtrationto followed by filtration under reduced pressure
  4. washThe toluene layer was washed with a common salt aqueous solution
  5. dry with materialby drying with anhydrous sodium sulfate
  6. customThen, the sodium sulfate was removed from the mixture
  7. customthe resultant mixture was evaporated
  8. customto obtain a residue
  9. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1)
  10. additiontreated with activated carbon
  11. customfollowed by recrystallization from acetone

Quellen und Nachweise

ORD-Eintrag
ord-3e619ec6b0d74da2b4a63b798c2150ab
Quelldatensatz
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05385692

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