Chlorosulfonyl isocyanate → 6-methoxy-2-methyl-1H-indole-3-carbonitrile

HRID 506020

Reaktionsgleichung

Reaktionsgleichung von HRID 506020
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([CH3:12])[NH:9]2)=[CH:5][CH:4]=1.ClS([N:17]=[C:18]=O)(=O)=O.C([O-])(O)=O.[Na+]>C(#N)C.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:18]#[N:17])=[C:8]([CH3:12])[NH:9]2)=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 70918Chlorosulfonyl isocyanateHCID 516892Sodium BicarbonateHCID 108447096-methoxy-2-methyl-1H-indole

Produkt 1

HCID 139046406-methoxy-2-methyl-1H-indole-3-carbonitrileAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a solution of 6-methoxy-2-methyl-1H-indole (3.9 g, 24 mmol) in acetonitrile (200 mL) and DMF (20 mL) is added dropwise a solution of ClSO2NCO (4 mL, 1.3 eq.) in acetonitrile (31 mL) at 0° C. After the addition, the mixture is stirred at room temperature for 3 h. Then it is poured into ice water and saturated NaHCO3 is added to it until it becomes basic. The aqueous phase is extracted with CH2Cl2 and then evaporated. The residue is purified with flash column chromatography on silica gel using EtOAc/petroleum ether (1/5) as eluent to yield 81% of 6-methoxy-2-methyl-1H-indole-3-carbonitrile.

Aufarbeitung

  1. additionAfter the addition
  2. additionis added to it until it
  3. extractionThe aqueous phase is extracted with CH2Cl2
  4. customevaporated
  5. customThe residue is purified with flash column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c7409b47bc23439c981f762c3d186901
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781478B2

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