Potassium Carbonate → HCID 11550771, Verbindung

HRID 1009540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009540
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH:16]=[O:17])=[CH:10][N:11]2[CH2:14][CH3:15])=[CH:7][CH:6]=1)=[O:4].CC1C=CC(S([CH2:28][N+:29]#[C-:30])(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+]>CO>[CH2:14]([N:11]1[C:12]2[C:8](=[CH:7][CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:13]=2)[C:9]([C:16]2[O:17][CH:30]=[N:29][CH:28]=2)=[CH:10]1)[CH3:15]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 59425156Methyl 1-ethyl-3-formyl-1H-indole-6-carboxylate

Produkt 1

HCID 11550771HCID 11550771, VerbindungAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1-Ethyl-3-formyl-1H-indole-6-carboxylic acid methyl ester (100 mg, 0.42 mmol), TOSMIC (100 mg, 0.52 mmol), K2CO3 (178 mg, 1.29 mmol), and MeOH (800 μL) are heated at 80° C. overnight. The reaction mixture is then partitioned between H2O and ether. After drying and concentrating the organic phase, the product is purified by silica gel chromatography (EtOAc/CH2Cl2, 10/90) to give methyl 1-ethyl-3-oxazol-5-yl-1H-indole-6-carboxylate (26 mg, 23%) as an off-white solid.

Aufarbeitung

  1. customThe reaction mixture is then partitioned between H2O and ether
  2. customAfter drying
  3. concentrationconcentrating the organic phase
  4. customthe product is purified by silica gel chromatography (EtOAc/CH2Cl2, 10/90)

Quellen und Nachweise

ORD-Eintrag
ord-7a087f8ae6ca4d8e813455b7ebf1537a
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973069B2

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