Indole-2-carboxylic acid → HCID 22676754, Verbindung

HRID 1006246Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1006246
N1[C:9]2[C:4](=[CH:5]C=CC=2)[CH:3]=C1C(O)=O.[Br:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C:15]=1[C:23]([OH:25])=[O:24].C(OC(OC(C)(C)C)N(C)C)(C)(C)C>C1(C)C=CC=CC=1>[Br:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C:15]=1[C:23]([O:25][C:4]([CH3:9])([CH3:5])[CH3:3])=[O:24]

Komponenten

5

Edukt 3

HCID 72899Indole-2-carboxylic acidHCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 23256883-bromo-1H-indole-2-carboxylic acid

Produkt 1

HCID 22676754HCID 22676754, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Indole-2-carboxylic acid was converted to 3-bromoindole-2-carboxylic acid using the method described for Example 13. N,N-dimethylformamide di-tert-butyl acetal (35 mL) was added dropwise to a stirring mixture of indole-3-bromo-2-carboxylic acid (14.9 g, 62 mmol) suspended in toluene (100 mL). After the addition was complete, the reaction was heated at 90° C. for 8 h. The reaction mixture was then cooled to room temperature and washed with cold water (2×100 mL). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to yield the crude tert-butyl 3-bromoindole-2-carboxylate, assume quantitative yield. The crude product was used in the next step without purification.

Aufarbeitung

  1. additionAfter the addition
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. washwashed with cold water (2×100 mL)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-86bb1b1400ff4981bb031d4cedf85771
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787651B2

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