Potassium Carbonate → HCID 86698613, Verbindung

HRID 1054609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1054609
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 2 N 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. MS (ES+) 447.0 (M+Na)+.

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-3a80c556e3324bbda87bfbfe6440e2a4
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394285B2

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