Tetrahydrofuran → 2-((4-(3-(4-Bromophenyl)benzo[d]isothiazol-6-yl)-2-methylbut-3-yn-2-yl)(ethyl)amino)ethanol
Reaktionsgleichung
C(OP(=O)(OCC)O[C:6]([CH3:26])([CH3:25])[C:7]#[C:8][C:9]1[CH:24]=[CH:23][C:12]2[C:13]([C:16]3[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=3)=[N:14][S:15][C:11]=2[CH:10]=1)C.[CH2:31]([NH:33][CH2:34][CH2:35][OH:36])[CH3:32].C1COCC1.C([O-])(O)=O.[Na+]>CCOC(C)=O>[Br:22][C:19]1[CH:18]=[CH:17][C:16]([C:13]2[C:12]3[CH:23]=[CH:24][C:9]([C:8]#[C:7][C:6]([N:33]([CH2:31][CH3:32])[CH2:34][CH2:35][OH:36])([CH3:25])[CH3:26])=[CH:10][C:11]=3[S:15][N:14]=2)=[CH:21][CH:20]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To 45 mg (0.09 mmol) Phosphoric acid 3-[3-(4-bromo-phenyl)-benzo[d]isothiazol-6-yl]-1,1-dimethyl-prop-2-ynyl ester diethyl ester and 16 μl (0.18 mmol) 2-Ethylaminoethanol in 0.5 ml THF 10.2 mg (0.01 mmol) tetrakis(triphenylphosphine)palladium was added and the suspension stirred at 50° C. over night. The mixture was added to a saturated aqueous solution of NaHCO3 and EtOAc, the phases were separated and the inorganic one was extracted with EtOAc. The combined organic phases were washed with brine and dried over Na2SO4. Column chromatography on silica gel with CH2Cl2:MeOH 95:5 gave 2-((3-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yl]-1,1-dimethyl-prop-2-ynyl)-ethyl-amino)-ethanol as yellow semisolid, MS: 443 (MH+, 1Br).
Aufarbeitung
- customthe phases were separated
- extractionthe inorganic one was extracted with EtOAc
- washThe combined organic phases were washed with brine
- dry with materialdried over Na2SO4
Quellen und Nachweise
- ORD-Eintrag
- ord-60ae6f6da48e4dd887c495929d4e673f
- Quelldatensatz
- uspto-grants-2007_02
- Patentnummer
- US07173043B2
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