4-Fluoroiodobenzene → Methyl 3-fluoro-1-(4-fluorophenyl)-1H-indole-6-carboxylate

HRID 468194

Reaktionsgleichung

Reaktionsgleichung von HRID 468194
[F:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:23][C:24]1[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=1.CNC1CCCCC1NC>CCOC(C)=O.O.[Cu]I.C1(C)C=CC=CC=1>[F:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[N:4]([C:27]2[CH:28]=[CH:29][C:24]([F:23])=[CH:25][CH:26]=2)[CH:3]=1

Komponenten

9

Edukt 4

HCID 96054-FluoroiodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 59625843methyl 3-fluoro-1H-indole-6-carboxylate

Produkt 1

HCID 59625701Methyl 3-fluoro-1-(4-fluorophenyl)-1H-indole-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

Compound 69a (0.264 mmol, 51 mg), CuI (0.0264 mmol, 5 mg) and K3PO4 (0.66 mmol, 40 mg) were combined in a sealed reaction tube and the vial was back-flushed with N2. 4-fluoro-iodobenzene 69b (0.264 mmol, 0.0394 mL) and N,N′-dimethylcyclohexane-1,2-diamine (0.0792 mmol, 0.0125 mL) were added via sringe, followed by toluene. The reaction mixture was heated at 95° C. for 6 h. The reaction was diluted with EtOAc and water. The reaction mixture was concentrated and purified by flash column chromatography (silica gel, 20% EtOAc/hexanes) to give compound 69c.

Aufarbeitung

  1. customthe vial was back-flushed with N2
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by flash column chromatography (silica gel, 20% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ebde23f4776249a38692f6bae74e5912
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623858B2

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