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Sodium Iodide → HCID 178527416, Verbindung

HRID 1433229
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1433229
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[S:23]([CH2:26][CH2:27][OH:28])(=[O:25])=[O:24])=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:29]Br)=O)(C)(C)C.[F:31][C:32]([F:44])([F:43])[S:33]([C:36]1[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=1)(=[O:35])=[O:34].C([O-])([O-])=O.[Na+].[Na+].[Na+].[I-]>CN(C=O)C>[F:44][C:32]([F:43])([F:31])[S:33]([C:36]1[CH:37]=[CH:38][C:39]([O:42][CH2:29][C:9]2[NH:8][C:12]3[CH:13]=[CH:14][C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[S:23]([CH2:26][CH2:27][OH:28])(=[O:25])=[O:24])=[CH:16][C:11]=3[N:10]=2)=[CH:40][CH:41]=1)(=[O:34])=[O:35]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 148574264-TrifluoromethanesulfonylphenolHCID 579349702-Bromomethyl-5-[2-(2-hydroxy-ethanesulfonyl)-phenyl]-benzoimidazole-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 178527416HCID 178527416, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-bromomethyl-5-[2-(2-hydroxy-ethanesulfonyl)-phenyl]-benzoimidazole-1-carboxylic acid tert-butyl ester (0.030 g, 0.0606 mmol), 4-trifluoromethanesulfonyl-phenol (0.027 g, 0.121 mmol), Na2CO3 (0.026 g, 0.242 mmol), and NaI (0.036 g, 0.242 mmol) in DMF (1 mL) was stirred for 12 hours at room temperature. The reaction mixture was concentrated under reduced pressure and the resulting residue was dissolved in CH2Cl2 (1 mL) followed by an addition of TFA (0.3 mL) and the mixture was stirred at rt for 3 hours. The reaction mixture was concentrated, and the residue was purified by chromatography (silica, CH2Cl2: MeOH, 5:1) to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD) δ (ppm): 8.17 (dd, 1H, J=8.0 Hz, J=1.2 Hz), 8.03 (d, 2H, J=8.8 Hz), 7.76-7.62 (m, 4H), 7.48-7.45 (m, 3H), 7.35 (d, 1H, J=8.4 Hz), 5.57 (s, 2H), 3.63 (t, 2H, J=6.4 Hz), 2.91 (t, 2H, J=6.6 Hz). Mass Spectrum (LCMS, ESI pos.) Calcd. For C25H23F3N3O6S2: 582.5 (M+MeCN+H), Found 582.2.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in CH2Cl2 (1 mL)
  3. additionfollowed by an addition of TFA (0.3 mL)
  4. stirringthe mixture was stirred at rt for 3 hours
  5. concentrationThe reaction mixture was concentrated
  6. customthe residue was purified by chromatography (silica, CH2Cl2: MeOH, 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-87ff647116264d0c889e5c605fc8c44a
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07612211B2

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