2-Iodotoluene → HCID 68940392, Verbindung

HRID 2199756Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2199756
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:17]=2[NH:16][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14]3)O1.F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[F-].[Cs+].I[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=1[CH3:51]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CO.O1CCOCC1>[C:46]1([CH3:51])[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=1[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14]2

Komponenten

8

Edukt 4

HCID 51282-IodotolueneHCID 25953Cesium fluorideHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 16050160Ethyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxylate

Produkt 1

HCID 68940392HCID 68940392, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 887MethanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a mixture of ethyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-2-carboxylate (Paul et al. J. Am. Chem. Soc. 2006, 128, 15552-15553) (1.6 g), tri-(t-butyl)phosphonium tetrafluoroborate (0.074 g), tris(dibenzylideneacetone)dipalladium(0) (0.116 g) and cesium fluoride (2.313 g) was added ortho-iodotoluene (0.781 ml), then dioxane (200 ml) and methanol (20 ml). The reaction mixture was immediately purged with nitrogen and stirred at room temperature for 2 hours. Additional amounts of (dibenzylideneacetone)dipalladium(0) (0.116 g), ortho-iodotoluene (0.781 ml), CsF (2.313 g), and tri-(t-butyl)phosphonium tetrafluoroborate (0.074 g) were added at the same time. The resulting solution was stirred at room temperature overnight. The insoluble material was filtered off and the filtrate was concentrated and the residue was purified by flash chromatography, eluting with 0-100% dichloromethane in hexane to provide the title compound.

Aufarbeitung

  1. customThe reaction mixture was immediately purged with nitrogen
  2. additionAdditional amounts of (dibenzylideneacetone)dipalladium(0) (0.116 g), ortho-iodotoluene (0.781 ml), CsF (2.313 g), and tri-(t-butyl)phosphonium tetrafluoroborate (0.074 g) were added at the same time
  3. stirringThe resulting solution was stirred at room temperature overnight
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated
  6. customthe residue was purified by flash chromatography
  7. washeluting with 0-100% dichloromethane in hexane

Quellen und Nachweise

ORD-Eintrag
ord-a733100975754e9c8b12cfb804ff773c
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359296B2

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