Sodium Carbonate → (2Benzo[1,2,5]oxadiazol-5-yl-phenyl)-dimethyl-amine

HRID 1867507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1867507
C([O-])(=O)C.[K+].Br[C:7]1[CH:8]=[CH:9][C:10]2[C:11]([CH:15]=1)=[N:12][O:13][N:14]=2.C(=O)([O-])[O-].[Na+].[Na+].Br[C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[N:25]([CH3:27])[CH3:26]>CN(C=O)C.O>[N:14]1[O:13][N:12]=[C:11]2[CH:15]=[C:7]([C:23]3[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=3[N:25]([CH3:27])[CH3:26])[CH:8]=[CH:9][C:10]=12

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 1365272-Bromo-N,N-dimethylanilineHCID 517044Potassium AcetateHCID 27762985-Bromo-2,1,3-benzoxadiazole

Produkt 1

HCID 68878349(2Benzo[1,2,5]oxadiazol-5-yl-phenyl)-dimethyl-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

523 mg (1.65 eq.) bis(pinacolato)diboran, 552 mg (4.5 eq.) potassium acetate and 51 mg (0.01 eq.) PdCl(dppf)-CH2Cl2 are added to a solution of 373 mg 5-bromo-benzo[1,2,5]oxadiazole in 8 mL DMF and heated to 80° C. under continuous stirring for 6 hours. 662 mg (5 eq.) sodium carbonate in 3.3 mL water are added together with 500 mg (1 eq.) 2-bromo-N,N-dimethylaniline and 51 mg (0.01 eq.) PdCl(dppf)-CH2Cl2 to the reaction mixture, which is stirred for another 18 hours at 80° C., cooled to room temperature and extracted with ethyl acetate and water. The combined organic phases are washed with brine, dried over magnesium sulfate and evaporated. The residue is column chromatographed (hexane, then hexane/ethyl acetate 8:1) to yield the desired product as an orange resin. MS(ES+): 240 (M+1).

Aufarbeitung

  1. stirringis stirred for another 18 hours at 80° C.
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl acetate and water
  4. washThe combined organic phases are washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customchromatographed (hexane

Quellen und Nachweise

ORD-Eintrag
ord-84c49cd67ec942568ab3dc4c0b137042
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07632851B2

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