Ammonia → 5-Fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide

HRID 1943985

Reaktionsgleichung

Reaktionsgleichung von HRID 1943985
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[C:6]([C:19]([OH:21])=O)=[CH:5]2.S(Cl)(Cl)=O.[NH3:26]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[C:6]([C:19]([NH2:26])=[O:21])=[CH:5]2

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 574315135-fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxylic acid

Produkt 1

HCID 668456965-Fluoro-1-(3-fluorobenzyl)-1H-indole-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a suspension, stirred at 20° C., of 2 g (6.96 mmol) of 5-fluoro-1-[(3-fluorophenyl)-methyl]-1H-indole-2-carboxylic acid, prepared in step 1.1, in 80 mL of dry toluene are added 5.08 mL (69.62 mmol) of thionyl chloride. The reaction mixture is refluxed for 2 hours with stirring and is then concentrated under reduced pressure. The resulting product is taken up in 10 mL of dichloromethane, and this solution is poured dropwise into a solution of 9.12 mL (69.62 mmol) of 30% aqueous ammonia. The reaction mixture is stirred for 14 hours at 20° C. After this time, a solid is collected by filtration, and is triturated in 50 mL of diisopropyl ether. After filtering off and drying under reduced pressure, 0.58 g of the expected product is collected.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 2 hours
  2. concentrationis then concentrated under reduced pressure
  3. stirringThe reaction mixture is stirred for 14 hours at 20° C
  4. filtrationAfter this time, a solid is collected by filtration
  5. customis triturated in 50 mL of diisopropyl ether
  6. filtrationAfter filtering off
  7. dry with materialdrying under reduced pressure, 0.58 g of the expected product
  8. customis collected

Quellen und Nachweise

ORD-Eintrag
ord-0c95923f5a964156bd34107648a0327a
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394820B2

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