Water → HCID 58392203, Verbindung

HRID 561583

Reaktionsgleichung

Reaktionsgleichung von HRID 561583
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)O)=[CH:4][CH:3]=1.[Cl-].[In+3].[Cl-].[Cl-].ClC1C=C(Cl)C=CC=1C([C:33]1[C:41]2[C:36](=[C:37]([CH2:43][S:44][CH3:45])[CH:38]=[C:39](F)[CH:40]=2)[NH:35][CH:34]=1)CCO.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:33]2[C:41]3[C:36](=[C:37]([CH2:43][S:44][CH3:45])[CH:38]=[CH:39][CH:40]=3)[NH:35][CH:34]=2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 159675indium(III)chlorideHCID 12634874(4-Chlorophenyl)(4-fluorophenyl)methanolHCID 583923053-(2,4-Dichlorophenyl)-3-{5-fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}propan-1-ol

Produkt 1

HCID 58392203HCID 58392203, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2.94 g (12.41 mmol) of the compound from Example 81A and 2.50 g (11.28 mmol) of indium(III) chloride were added to 2.00 g (11.28 mmol) of the compound from Example 8 in 100 ml of toluene. The reaction mixture was stirred at 80° C. for 3 h. After cooling to RT, the reaction solution was mixed with water and ethyl acetate and the solid was filtered off. The phases of the filtrate were separated, and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated. Purification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient) resulted in 0.83 g (19% of theory) of the title compound.

Aufarbeitung

  1. temperatureAfter cooling to RT
  2. filtrationthe solid was filtered off
  3. customThe phases of the filtrate were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the crude product by preparative HPLC (mobile phase: acetonitrile/water gradient)

Quellen und Nachweise

ORD-Eintrag
ord-f82843f8ab13408c9b2b316e0f3d0001
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063234B2

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