Carbon Dioxide → 5-chloro-1H-indole-7-carboxylic acid

HRID 2243171

Reaktionsgleichung

Reaktionsgleichung von HRID 2243171
Br[C:2]1[CH:3]=[C:4]([Cl:11])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.C([Li])CCC.[C:17](=[O:19])=[O:18].O>C1COCC1.CCCCCC>[Cl:11][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([C:17]([OH:19])=[O:18])[CH:3]=1)[NH:9][CH:8]=[CH:7]2

Komponenten

7

Edukt 4

HCID 280Carbon DioxideHCID 962WaterHCID 247295047-bromo-5-chloro-1H-indoleHCID 178418339Butyllithium

Produkt 1

HCID 668685635-chloro-1H-indole-7-carboxylic acidAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

1.15 g (5 mmol) of 7-bromo-5-chloro-1H-indole were dissolved in 30 ml THF. At −75° C. under argon 9.4 ml (15 mmol) of a 1.6 M n-butyllithium solution in hexane were added dropwise. After complete addition the reaction mixture was stirred at 5° C. for 30 min, cooled to −75° C. and 10 g dry ice was added. The reaction mixture was warmed to RT and stirred for 15 min. It was poured onto 100 ml of water and extracted twice with ethyl acetate. The aqueous layer was acidified with 1N aqueous HCl solution and extracted twice with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered and the solvent was evaporated. The residue was treated with hexane and stirred for 10 min. The precipitate was filtered, washed with hexane and dried to yield 700 mg (72%) of 5-chloro-1H-indole-7-carboxylic acid as a white solid. MS (ISP) 194.0 (M−H)−.

Aufarbeitung

  1. additionAfter complete addition the reaction mixture
  2. temperaturecooled to −75° C.
  3. temperatureThe reaction mixture was warmed to RT
  4. stirringstirred for 15 min
  5. extractionextracted twice with ethyl acetate
  6. extractionextracted twice with dichloromethane
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. additionThe residue was treated with hexane
  11. stirringstirred for 10 min
  12. filtrationThe precipitate was filtered
  13. washwashed with hexane
  14. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0fcddc8c3a364a78a6c40bc92ba46b04
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07674815B2

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