Potassium Carbonate → HCID 86698613, Verbindung

HRID 338266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338266
CC1(C)COB([C:8]2[CH:13]=[CH:12][C:11]([CH:14]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15]3)=[CH:10][CH:9]=2)OC1.Br[C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][C:36]=1[Cl:37])[NH:33][CH:32]=[C:31]2[CH:38]=[O:39].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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:37][C:36]1[CH:35]=[C:34]2[C:30]([C:31]([CH:38]=[O:39])=[CH:32][NH:33]2)=[CH:29][C:28]=1[C:8]1[CH:9]=[CH:10][C:11]([CH:14]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:15]2)=[CH:12][CH:13]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 866985665-bromo-6-chloro-1H-indole-3-carbaldehydeHCID 86698612tert-Butyl 3-(4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl)pyrrolidine-1-carboxylate

Produkt 1

HCID 86698613HCID 86698613, VerbindungAusbeute 39,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a degassed mixture of tert-butyl 3-[4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyl]pyrrolidine-1-carboxylate (85 mg, 0.237 mmol), 5-bromo-6-chloro-1H-indole-3-carbaldehyde (67.3 mg, 0.26 mmol) and 2N aqueous potassium carbonate (0.47 mL, 0.94 mmol) in toluene (1.12 mL) and ethanol (0.38 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (17.3 mg, 0.0237 mmol). The reaction mixture was heated to 120° C. in a microwave for 30 min. The reaction mixture was partitioned between water and EtOAc. The EtOAc layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (EtOAc/petroleum ether=1:2) to give tert-butyl 3-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenyl]pyrrolidine-1-carboxylate (40 mg) as a yellow solid.

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. washThe EtOAc layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative thin-layer chromatography (EtOAc/petroleum ether=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-c98561e69ac743cfb09441384d348b08
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889730B2

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