Potassium Carbonate → 6-chloro-5-[4-(1-methylpyrrolidin-3-yl)phenyl]-1H-indole-3-carbaldehyde

HRID 338402

Reaktionsgleichung

Reaktionsgleichung von HRID 338402
[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:22])([O-])[O-].[K+].[K+].Br[C:26]1[CH:31]=[CH:30][C:29]([CH:32]2[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33]2)=[CH:28][CH:27]=1>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:22])=[CH:7][NH:8]2)=[CH:4][C:3]=1[C:26]1[CH:27]=[CH:28][C:29]([CH:32]2[CH2:36][CH2:35][N:34]([CH3:37])[CH2:33]2)=[CH:30][CH:31]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 594284273-(4-Bromophenyl)-1-methylpyrrolidineHCID 866987336-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole

Produkt 1

HCID 866987406-chloro-5-[4-(1-methylpyrrolidin-3-yl)phenyl]-1H-indole-3-carbaldehydeAusbeute 152,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Versuchsvorschrift

To 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (118 mg, 0.446 mmol) in anhydrous 1,4-dioxane (3.7 mL) and anhydrous DMF (0.74 mL) was added N,N-dimethylformiminium chloride (114 mg, 0.892 mmol). The reaction mixture was stirred for 10 min at room temperature, yielding a thick suspension. The reaction mixture was treated with 2N aqueous potassium carbonate (1.1 mL, 2.2 mmol), 3-(4-bromophenyl)-1-methylpyrrolidine (120 mg, 0.446 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (26 mg, 0.036 mmol). The resulting mixture was heated at 90° C. for 30 min. The reaction mixture was cooled and partitioned between water and EtOAc. The aqueous phase was extracted twice with EtOAc, and the combined organic phases were dried over sodium sulfate and concentrated in vacuo to give 6-chloro-5-[4-(1-methylpyrrolidin-3-yl)phenyl]-1H-indole-3-carbaldehyde (0.23 g, 16% yield) which was used directly in the next step. MS (ES+) 339.0 (M+H)+.

Aufarbeitung

  1. customyielding a thick suspension
  2. temperatureThe resulting mixture was heated at 90° C. for 30 min
  3. temperatureThe reaction mixture was cooled
  4. custompartitioned between water and EtOAc
  5. extractionThe aqueous phase was extracted twice with EtOAc
  6. dry with materialthe combined organic phases were dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0d660c52160d407ab2ca323f19e861c1
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889730B2

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