Potassium Carbonate → 6-Chloro-5-phenyl-1H-indole-3-carbaldehyde

HRID 338221

Reaktionsgleichung

Reaktionsgleichung von HRID 338221
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][CH:6]=[C:5]2[CH:12]=[O:13].[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CCO.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:11][C:10]1[CH:9]=[C:8]2[C:4]([C:5]([CH:12]=[O:13])=[CH:6][NH:7]2)=[CH:3][C:2]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 866985665-bromo-6-chloro-1H-indole-3-carbaldehyde

Produkt 1

HCID 866985726-Chloro-5-phenyl-1H-indole-3-carbaldehydeAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-6-chloro-1H-indole-3-carbaldehyde (200 mg, 0.77 mmol), phenyl boronic acid (114 mg, 0.93 mmol), 2N aqueous potassium carbonate (1.15 mL, 3.10 mmol) in toluene (3.3 mL) and EtOH (1.1 mL) was degassed with N2, treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (56.6 mg, 0.077 mmol), and degassed again with N2. The mixture was subjected to microwave irradiation conditions at 120° C. for 30 minutes. The reaction mixture was cooled to room temperature, diluted with water and extracted with EtOAc (50 mL). The organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (0-46% EtOAc/petroleum ether) to afford the title compound (190 mg, 98% yield) as a yellow solid.

Aufarbeitung

  1. customwas degassed with N2
  2. customdegassed again with N2
  3. customirradiation conditions at 120° C. for 30 minutes
  4. additiondiluted with water
  5. extractionextracted with EtOAc (50 mL)
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe crude material was purified by flash chromatography (0-46% EtOAc/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-bc14fd9a3671457d8e8bfb84eb9723b6
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889730B2

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