Potassium Carbonate → diethyl 1-(cyanomethyl)-1H-indole-2,6-dicarboxylate

HRID 1748252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748252
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=2)[CH:3]=[C:2]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].C([O-])([O-])=O.[K+].[K+].Br[CH2:27][C:28]#[N:29]>CN(C=O)C.CCOC(C)=O>[C:28]([CH2:27][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:8]=2)[CH:3]=[C:2]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:29]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate2×

Produkt 1

HCID 58767564diethyl 1-(cyanomethyl)-1H-indole-2,6-dicarboxylateAusbeute 84,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of diethyl 1H-indole-2,6-dicarboxylate (Intermediate A, 4.0 g, 15.3 mmol) in dry DMF (50 mL) is added K2CO3 (6.3 g, 45.9 mmol). The reaction mixture is stirred under N2 for 30 min. Bromoacetonitrile (2.1 mL, 30.6 mmol) is added and the reaction mixture is heated to 80° C. for 4 h. After cooling, the reaction mixture is taken up in EtOAc (300 mL) and washed with water, then brine, dried (Na2SO4) and concentrated. The residue is recrystallized from ethanol to afford the title compound (3.9 g, 84%) as fine off-white needles.

Aufarbeitung

  1. temperatureAfter cooling
  2. washwashed with water
  3. dry with materialbrine, dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue is recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-9a3a139b627f4532b5db0026244479b1
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150577B2

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