Iodoethane → 1-Ethyl-6-trifluoromethoxyindole-3-carbonitrile

HRID 1009637Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009637
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1.ClS([N:19]=[C:20]=O)(=O)=O.C([O-])([O-])=O.[K+].[K+].[CH2:28](I)[CH3:29]>CN(C=O)C>[CH2:28]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([O:3][C:2]([F:1])([F:13])[F:14])[CH:12]=2)[C:8]([C:20]#[N:19])=[CH:9]1)[CH3:29]

Komponenten

6

Edukt 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 70918Chlorosulfonyl isocyanateHCID 220489586-(Trifluoromethoxy)-1H-indole

Produkt 1

HCID 594258351-Ethyl-6-trifluoromethoxyindole-3-carbonitrileAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-trifluoromethoxyindole (2.68 g, 13.3 mmol) in dry DMF (10 mL) at 0° C., is added chlorosulfonylisocyanate (2.35 g, 1.44 mL, 16.6 mmol). The mixture is then brought to room temperature slowly and stirred for 1 h. The mixture is poured into ice (100 mL) and stirred for 1 h. The precipitate is collected by filtration and washed thoroughly with water and dried in vacuo, which is then dissolved in DMF (15 mL). To the solution is added K2CO3 and EtI (2.59 g, 1.34 mL, 16.6 mmol), and the mixture is stirred at 50° C. overnight. It is then poured into ice-water (200 mL). The precipitate is collected by filtration and washed with water, dried in air and purified by chromatography (silica gel, DCM) to furnish 1-ethyl-6-trifluoromethoxyindole-3-carbonitrile (2.90 g, 86%).

Aufarbeitung

  1. customis then brought to room temperature
  2. stirringstirred for 1 h
  3. filtrationThe precipitate is collected by filtration
  4. washwashed thoroughly with water
  5. customdried in vacuo, which
  6. dissolutionis then dissolved in DMF (15 mL)
  7. stirringthe mixture is stirred at 50° C. overnight
  8. filtrationThe precipitate is collected by filtration
  9. washwashed with water
  10. customdried in air
  11. custompurified by chromatography (silica gel, DCM)

Quellen und Nachweise

ORD-Eintrag
ord-a0ed4a77f81b48e58b1523a4d64344de
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973069B2

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