Water → 6-chloro-5-{4-[2-(morpholin-4-yl)-2-oxoethyl]phenyl}-1H-indole-3-carbaldehyde

HRID 338408

Reaktionsgleichung

Reaktionsgleichung von HRID 338408
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1B1OCC(C)(C)CO1.[C:19](=O)([O-])[O-:20].[K+].[K+].Br[C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)=[O:34])=[CH:28][CH:27]=1.O>O1CCOCC1.CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH:19]=[O:20])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)=[O:34])=[CH:28][CH:27]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 8758802-(4-Bromophenyl)-1-morpholinoethanoneHCID 866987336-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole

Produkt 1

HCID 866987456-chloro-5-{4-[2-(morpholin-4-yl)-2-oxoethyl]phenyl}-1H-indole-3-carbaldehydeAusbeute 112,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (153 mg, 0.581 mmol) in anhydrous 1,4-dioxane (5 mL) and DMF (1 mL) was added N,N-dimethylformiminium chloride (160 mg, 1.25 mmol). The reaction mixture was stirred at room temperature for 20 minutes, and then treated with 2N aqueous potassium carbonate (1.44 mL, 2.90 mmol) and 2-(4-bromophenyl)-1-(morpholin-4-yl)ethanone (165 mg, 0.58 mmol). The reaction was degassed with nitrogen, and treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (50 mg, 0.068 mmol). The reaction mixture was stirred at 90° C. for 30 minutes, cooled to room temperature, and poured into water (15 mL). The product was extracted with ethyl acetate (3×20 mL), and the combined organic phases were dried and concentrated in vacuo to give the title compound (249 mg, >100% yield) as a red solid, which was used in the next step without further purification.

Aufarbeitung

  1. customThe reaction was degassed with nitrogen
  2. stirringThe reaction mixture was stirred at 90° C. for 30 minutes
  3. temperaturecooled to room temperature
  4. extractionThe product was extracted with ethyl acetate (3×20 mL)
  5. customthe combined organic phases were dried
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1cbf5c481c744a82ac133d4a164707d5
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889730B2

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