Triphenylphosphine → methyl 2-(2,6-dimethylphenyl)-1H-indole-6-carboxylate

HRID 1514930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1514930
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]#[C:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=1[NH:21]C(=O)C(F)(F)F.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[NH:21][C:12]2[C:11]([CH:10]=1)=[CH:20][CH:19]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2

Komponenten

6

Edukt 3

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 86651266Methyl 4-(2,6-dimethylphenylethynyl)-3-(2,2,2-trifluoroacetylamino)-benzoate

Produkt 1

HCID 66966102methyl 2-(2,6-dimethylphenyl)-1H-indole-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

A mixture of methyl 4-(2,6-dimethylphenylethynyl)-3-(2,2,2-trifluoroacetylamino)-benzoate (103 mg, 270 μmol), copper (I) iodide (2 mg, 10 μmol), triphenylphosphine (6 mg, 23 μmol), and K3PO4 (117 mg, 550 μmol) in dioxane (2 mL) was heated at 115° C. in a microwave apparatus for 15 min. The solution was concentrated, then chromatographed using a gradient of 0-40% heptane/ethyl acetate to afford methyl 2-(2,6-dimethylphenyl)-1H-indole-6-carboxylate.

Aufarbeitung

  1. concentrationThe solution was concentrated
  2. customchromatographed

Quellen und Nachweise

ORD-Eintrag
ord-be20f2bccbf9495ba20d5cf6beefd489
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222248B2

Notizen zur Reaktion

Wird geladen…