Triethylamine → 4-oxo-8-trimethylsilanylethynyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

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Reaktionsgleichung

C(N(CC)CC)C.I[C:9]1[CH:18]=[CH:17][C:16]2[NH:15][C:14](=[O:19])[C:13]3[NH:20][CH:21]=[CH:22][C:12]=3[C:11]=2[CH:10]=1.[CH2:23]([C:25]([O-:27])=[O:26])[CH3:24].[C:28]([Si:30]([CH3:33])([CH3:32])[CH3:31])#[CH:29]>O1CCOCC1.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:19]=[C:14]1[C:13]2[NH:20][CH:21]=[CH:22][C:12]=2[C:11]2[CH:10]=[C:9]([C:29]#[C:28][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:18]=[CH:17][C:16]=2[NH:15]1.[CH2:23]([C:25]([O-:27])=[O:26])[CH3:24]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

224 mg (1.2 mmol) of copper iodide, 309 mg (3 mmol) of triethylamine and 165 mg (0.23 mmol) of dichlorobis(triphenylphosphine)-palladium (11) are added to a suspension of 898 mg (2.35 mmol) of 8-iodo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 30 ml of anhydrous dioxan then this mixture is degassed under argon. After 15 minutes, 346 mg (3.52 mmol) of ethynyl-trimethyl-silane is added and the reaction mixture is heated at 100° C. for 3 hours. The raw reaction product is filtered on celite, then the filtrate is evaporated to dryness and the residue is purified on silica (eluent ethyl acetate) to give 400 mg (48%) of 4-oxo-8-trimethylsilanylethynyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a yellow solid.

Aufarbeitung

customthis mixture is degassed under argon
customThe raw reaction product
filtrationis filtered on celite
customthe filtrate is evaporated to dryness
customthe residue is purified on silica (eluent ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-07bb015719984c8490b42d065f58ed3b
Quelldatensatz: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08426437B2

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