Potassium Hydroxide → 7-Bromo-4-fluoroindoline

HRID 387311Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 387311
[BH3-]C#N.[Na+].[Br:5][C:6]1[CH:7]=[CH:8][C:9]([F:15])=[C:10]2[C:14]=1[NH:13][CH:12]=[CH:11]2.[OH-].[K+].C([O-])(O)=O.[Na+]>C(O)(=O)C.CCOC(C)=O>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([F:15])=[C:10]2[C:14]=1[NH:13][CH2:12][CH2:11]2

Komponenten

7

Edukt 4

HCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 43429567-bromo-4-fluoro-1H-indoleHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 593325897-Bromo-4-fluoroindoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

NaCNBH3 (2.4 g, 38.2 mmol) was added portionwise to a solution of 7-bromo-4-fluoro-1H-indole (1 g, 4.7 mmol) in acetic acid at −10° C. (bath temp). The reaction was stirred overnight, cooled to 0° C. (bath temp), and solid KOH was added. Saturated NaHCO3 and EtOAc were added, the layers were separated, and the organic layer evaporated. The crude product was purified by flash chromatography, giving the title compound.

Aufarbeitung

  1. additionwas added
  2. customthe layers were separated
  3. customthe organic layer evaporated
  4. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a87c10de7ae3417b81d91249abf5c8ea
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372875B2

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