HCID 10093591, Verbindung → 5-[(3-Ethyl-5-(2-[3-(methylsulfonyl)phenoxy]ethyl]-1H-pyrazol-4-yl)oxy]isophthalonitrile

HRID 1352718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1352718
[CH2:1]([C:3]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([C:17]#[N:18])[CH:12]=[C:13]([CH:16]=2)[C:14]#[N:15])=[C:6]([CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([S:28]([CH3:30])=[O:29])[CH:23]=2)[NH:5][N:4]=1)[CH3:2].[OH:31]OS([O-])=O.[K+]>CO.O>[CH2:1]([C:3]1[C:7]([O:8][C:9]2[CH:10]=[C:11]([C:17]#[N:18])[CH:12]=[C:13]([CH:16]=2)[C:14]#[N:15])=[C:6]([CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([S:28]([CH3:30])(=[O:31])=[O:29])[CH:23]=2)[NH:5][N:4]=1)[CH3:2]

Komponenten

5

Edukt 2

HCID 10093591HCID 10093591, VerbindungHCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 100945615-[(3-Ethyl-5-(2-[3-(methylsulfonyl)phenoxy]ethyl]-1H-pyrazol-4-yl)oxy]isophthalonitrileAusbeute 34,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of the sulfoxide from Example 5 (34 mg, 0.08 mmol) in methanol (1 ml) was added a solution of oxone (49 mg, 0.08 mmol) in water (1 ml). After 2 hours the reaction mixture was concentrated under reduced pressure and the residue was partitioned between dichloromethane (5 ml) and water (5 ml). The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product mixture was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (100:0, 99:1 then 98:2, by volume) to give the title compound as a colourless oil (12 mg).

Aufarbeitung

  1. concentrationAfter 2 hours the reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between dichloromethane (5 ml) and water (5 ml)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product mixture was purified by flash chromatography on silica gel eluting with dichloromethane:methanol (100:0, 99:1

Quellen und Nachweise

ORD-Eintrag
ord-3eb6d4de358c4d4abf8990cf23fbbb4d
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220772B2

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