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Isopropanol → 1-Benzenesulphonyl-5-methoxy-3-[(2-pyrrolidin-1-yl)ethyl]-1H-indole Hydrogen Oxalate

HRID 635382
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 635382
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[C:12]([CH2:21][CH2:22][O:23]S(C3C=CC=CC=3)(=O)=O)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:33](=[O:36])([O-:35])[O-].[K+].[K+].[NH:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1.CC([OH:47])C>>[C:22]([OH:23])(=[O:47])[C:33]([OH:35])=[O:36].[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[C:12]([CH2:21][CH2:22][N:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
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Komponenten

5

Edukt 4

HCID 3776Isopropanol2×HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 11762460benzenesulphonic acid 2-(1-benzenesulphonyl-5-methoxy-1H-indol-3-yl)ethyl ester

Produkt 1

HCID 212585631-Benzenesulphonyl-5-methoxy-3-[(2-pyrrolidin-1-yl)ethyl]-1H-indole Hydrogen OxalateAusbeute 65 %

Versuchsvorschrift

To a stirred solution of benzenesulphonic acid 2-(1-benzenesulphonyl-5-methoxy-1H-indol-3-yl)ethyl ester (0.191 g, 0.405 mmol) in anhydrous 2-propanol (10 ml) under nitrogen was added anhydrous potassium carbonate (0.112 g, 0.810 mmol), then a solution of pyrrolidine (0.17 ml, 2.03 mmol) in anhydrous 2-propanol (3 ml). The mixture was heated at reflux for 4 h, and the solvents were then removed in vacuo. The residue was partitioned between dichloromethane and water, and the aqueous layer was extracted further with dichloromethane. The combined organic extracts were washed with brine (2×25 ml), dried (Na2SO4), and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, CH2Cl2—MeOH—NH3; 95:5:0.5) to give 0.102 g (65%) of the title compound free base. The oxalate salt was prepared in EtOH-Et2O as a white solid; mp 217°-220° C.; δH (360 MHz, d6-DMSO) 1.94 (4H, s), 3.03 (2H, m), 3.27 (4H, s), 3.40 (2H, m), 3.79 (3H, s), 6.98 (1H, dd, J=9.0, 2.3 Hz), 7.17 (1H, d, J=2.3 Hz), 7.58 (2H, t, J=8.0 Hz), 7.69 (2H, m), 7.82 (1H, d, J=9.0 Hz), 7.92 (2H, d, J=7.9 Hz); m/z (ES+) 385 (MH30 ). Found: C, 57.83; H, 5.31; N, 5.87. C21H24N2O3S.C2H2O4 requires C, 58.22; H, 5.52; N, 5.90%.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 h
  3. customthe solvents were then removed in vacuo
  4. customThe residue was partitioned between dichloromethane and water
  5. extractionthe aqueous layer was extracted further with dichloromethane
  6. washThe combined organic extracts were washed with brine (2×25 ml)
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo
  9. customThe residue was purified by flash chromatography (silica gel, CH2Cl2—MeOH—NH3; 95:5:0.5)

Quellen und Nachweise

ORD-Eintrag
ord-811ee4f4c3e6424b99addb7617f0a8f3
Quelldatensatz
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06187805B1

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