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Sodium Carbonate → HCID 23585105, Verbindung

HRID 737078
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 737078
Br[C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][O:10][CH:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8]2)=[CH:4][CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].C(=O)([O-])[O-].[Na+].[Na+].[Cl:50][C:51]1[S:52][CH:53]=[CH:54][C:55]=1Br>CN(C=O)C.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>[Cl:50][C:51]1[S:52][CH:53]=[CH:54][C:55]=1[C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][O:10][CH:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:8]2)=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 27245593-Bromo-2-chlorothiopheneHCID 2733548Bis(pinacolato)diboraneHCID 578495044-(4-Bromo-benzyl)-2-phenyl morpholine

Produkt 1

HCID 23585105HCID 23585105, Verbindung
Ausbeute 10,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

91 mg of 4-(4-Bromo-benzyl)-2-phenyl-morpholine was combined with 77 mg of bis(pinacolato)diboron, 81 mg of potassium acetate, 16 mg tetrakis(triphenylphosphine)palladium(0), and 1.9 mL DMF. The mixture was heated in a microwave reactor at 120° C. for 7 minutes and cooled. 0.7 mL of 2M aqueous sodium carbonate was added along with 81 mg of 2-Chloro-3-bromothiophene in 0.12 mL DMF. The mixture was heated in the microwave reactor for an additional 5 minutes at 120° C. The reaction was cooled and filtered through Celite, washing with methylene chloride. The residue was diluted with 4 mL DCM and 130 mg of MP-TsOH resin (4.2 mmol/g loading) was added and the mixture agitated at room temperature overnight. The solution is filtered and the resin is then washed with 2M N3 in methanol to liberate product. The resin is washed several times with methylene chloride, concentrated in vacuo and purified by reverse phase HPLC. 10.9 mg of product is obtained as oil, 10% yield. ES MS m/z 398

Aufarbeitung

  1. temperaturecooled
  2. temperatureThe mixture was heated in the microwave reactor for an additional 5 minutes at 120° C
  3. temperatureThe reaction was cooled
  4. filtrationfiltered through Celite
  5. washwashing with methylene chloride
  6. additionThe residue was diluted with 4 mL DCM and 130 mg of MP-TsOH resin (4.2 mmol/g loading)
  7. additionwas added
  8. filtrationThe solution is filtered
  9. washthe resin is then washed with 2M
  10. washThe resin is washed several times with methylene chloride
  11. concentrationconcentrated in vacuo
  12. custompurified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-cb91a9bf78d0480581044e3c7ee394c6
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07595397B2

Notizen zur Reaktion

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