Potassium Carbonate → 3-{3-[2-(4-Methyl-piperidin-1-yl)-ethoxy]-phenyl}-thieno[2,3-d]isoxazole

HRID 8678

Reaktionsgleichung

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][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>C(#N)C>[CH3:25][CH:26]1[CH2:31][CH2:30][N:29]([CH2:2][CH2:3][O:4][C:5]2[CH:6]=[C:7]([C:11]3[C:15]4[S:16][CH:17]=[CH:18][C:14]=4[O:13][N:12]=3)[CH:8]=[CH:9][CH:10]=2)[CH2:28][CH2:27]1

Komponenten

Reaktionsbedingungen

Temperatur: 75 °C

Versuchsvorschrift

Mix 3-[3-(2-bromo-ethoxy)-phenyl]-thieno[2,3-d]isoxazole (0.250 g, 0.77 mmol), potassium carbonate (0.22 g, 1.59 mmol), 4-methylpiperidine (0.382 g, 3.85 mmol) and acetonitrile (4.0 mL) and heat at 75° C., overnight. Cool the reaction mixture and filter through a Waters Sep-Pak 1 g silica cartridge (ethyl acetate). Combine the appropriate fractions and concentrate to give a residue. Purify the residue by column (10 g silica) chromatography using a solvent gradient of dichloromethane to 10% methanol in dichloromethane to obtain the title compound (0.254 g, 96% Yield) as an amber oil. Purity by LC/MS (APCI)=99%, [M+H]+=343.

Aufarbeitung

temperatureCool the reaction mixture
filtrationfilter through a Waters Sep-Pak 1 g silica cartridge (ethyl acetate)
concentrationCombine the appropriate fractions and concentrate
customto give a residue
customPurify the residue by column (10 g silica) chromatography

Quellen und Nachweise

ORD-Eintrag: ord-f27a956677fb4f649e90173553ade153
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07091199B1

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