Potassium Carbonate → (2-Methoxy-benzyl)-[2-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-ethyl]-amine

HRID 8657

Reaktionsgleichung

Reaktionsgleichung von HRID 8657
Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:11]2[C:15]3[S:16][CH:17]=[CH:18][C:14]=3[O:13][N:12]=2)[CH:8]=[CH:9][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:25][O:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29][NH2:30]>C(#N)C>[CH3:25][O:26][C:27]1[CH:34]=[CH:33][CH:32]=[CH:31][C:28]=1[CH2:29][NH:30][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[C:15]3[S:16][CH:17]=[CH:18][C:14]=3[O:13][N:12]=2)[CH:6]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 812922-MethoxybenzylamineHCID 219835823-[3-(2-Bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole

Produkt 1

HCID 21983563(2-Methoxy-benzyl)-[2-(3-thieno[2,3-d]isoxazol-3-yl-phenoxy)-ethyl]-amineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Mix 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole (0.324 g, 1 mmol), potassium carbonate (0.28 g, 2 mmol), 2-methoxybenzylamine (0.686 g, 5 mmol) and acetonitrile (anhydrous, 4 mL) and heat at 75° C. for 16.5 hours. Cool the reaction mixture and filter through a Waters Sep-Pak silica gel cartridge (1 g) using ethyl acetate. Combine the appropriate fractions and concentrate to give a residue. Purify the residue by column (10 g silica) chromatography using a step gradient of 60% ethyl acetate in heptane to 100% ethyl acetate to give the title compound (342 mg, 90% Yield). Purity by LC/MS (APCI)=99%, [M+H]+=381.

Aufarbeitung

  1. temperatureCool the reaction mixture
  2. filtrationfilter through a Waters Sep-Pak silica gel cartridge (1 g)
  3. concentrationconcentrate
  4. customto give a residue
  5. customPurify the residue by column (10 g silica) chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7a23060077fa4a118beecc9e547f6e26
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091199B1

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