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Sodium Carbonate → HCID 21830737, Verbindung

HRID 1600931
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1600931
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=1)[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12].[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][CH2:30][CH:31]([O:43][Si](C(C)(C)C)(C)C)[CH2:32][O:33][C:34]2[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=2)[CH:24]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.[Cl-].[Na+].O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C.C1(C)C=CC=CC=1>[C:14]1([NH:13][C:11]([C:10]2[CH:9]=[C:8]([C:37]3[CH:36]=[CH:35][C:34]([O:33][CH2:32][CH:31]([OH:43])[CH2:30][CH2:29][C:25]4[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=4)=[CH:39][CH:38]=3)[CH:22]=[CH:21][CH:20]=2)=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 10340Sodium CarbonateHCID 8536523-bromo-N-phenylbenzamideHCID 2724141Tetrabutylammonium FluorideHCID 21717159HCID 21717159, Verbindung

Produkt 1

HCID 21830737HCID 21830737, VerbindungAusbeute 11,8 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 702EthanolLösungsmittel
HCID 1140TolueneLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel
HCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Prepared according to the method described in Example 33a) from toluene (3 ml), aqueous sodium carbonate (2 M, 0.9 ml), ethanol (1.0 ml), 3-bromo-N-phenylbenzamide (0.48 g), (±)-4-[4-(3-pyridyl)-2-(tert-butyldimethylsilyloxy)butoxy]benzeneboronic acid (0.7 g) and tetrakis(triphenylphosphine)palladium(0) (50 mg) with heating at 120° C. for 5 hours. The residue obtained after work up was purified by column chromatography over silica eluting with ethyl acetate:hexane (1:1) to give a colourless oil which was desilylated by treatment with tetrabutylammonium fluoride (0.7 ml; 1 M in tetrahydrofuran) in tetrahydrofuran at 0° C. After stirring at this temperature for 5 minutes a saturated solution of brine (5 ml) was added and the organic phase separated. The aqueous phase was extracted with ethyl acetate (20 ml). The combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethanol:dichloromethane (1:19) to give the title compound as a colourless solid (0.09 g).

Aufarbeitung

  1. customPrepared
  2. customThe residue obtained after work
  3. customup was purified by column chromatography over silica eluting with ethyl acetate:hexane (1:1)
  4. customto give a colourless oil which
  5. additionwas added
  6. customthe organic phase separated
  7. extractionThe aqueous phase was extracted with ethyl acetate (20 ml)
  8. washThe combined organic phases were washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by column chromatography over silica eluting with ethanol:dichloromethane (1:19)

Quellen und Nachweise

ORD-Eintrag
ord-b145db7797f948bf9d93d8b542ee30d9
Quelldatensatz
uspto-grants-1999_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05977105

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