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Sodium Carbonate → HCID 11618006, Verbindung

HRID 1445869
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1445869
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:21])=[C:11]([CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][C@H:16]3[CH3:20])[N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:28]([C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1)(=[O:30])[CH3:29]>C1(C)C=CC=CC=1.O.C(O)C.[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>[CH3:21][C:10]1[O:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:34]3[CH:35]=[CH:36][C:31]([C:28](=[O:30])[CH3:29])=[CH:32][CH:33]=3)=[CH:3][CH:4]=2)=[N:12][C:11]=1[CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH3:20]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 37021224-Acetylphenylboronic acidHCID 11530378HCID 11530378, Verbindung

Produkt 1

HCID 11618006HCID 11618006, VerbindungAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 702EthanolLösungsmittel
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(4-Bromo-phenyl)-5-methyl-4-[2-((R)-2-methyl-pyrrolidin-1-yl)-ethyl]-oxazole (100 mg, 0.287 munol), sodium carbonate (91 mg, 0.860 mmol) and 4-acetylphenyl boronic acid (235 mg, 1.43 mmol) in toluene (5 mL), water (1 mL) and ethanol (1.5 mL) under nitrogen is added Tetrakis (triphenylphosphine) palladium (0) (33.1 mg, 0.029 mmol). The reaction is heated at reflux for 48 h. The reaction is allowed to cool and bound to a SCX-2 cartridge (10 g). The cartridge is washed with one cartridge volumes of dimethylformamide and two volume of methanol. The product is eluted using 2M ammonia in methanol. The ammonia/methanol solution is evaporated on a Genevac® HT4. The sample is further purified by prep-LCMS. The resulting acetonitrile/water fractions are combined and evaporated using a Genevac® HT4 to give 62 mg of a colourless oil (56%). MS (m/e) 389.2 (M+1)

Aufarbeitung

  1. temperatureThe reaction is heated
  2. temperatureat reflux for 48 h
  3. temperatureto cool
  4. washThe cartridge is washed with one cartridge volumes of dimethylformamide and two volume of methanol
  5. washThe product is eluted
  6. customThe ammonia/methanol solution is evaporated on a Genevac® HT4
  7. customThe sample is further purified by prep-LCMS
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a5cdbd9fdfef4eed92a95e8f55b6ca0e
Quelldatensatz
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07666871B2

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