Triethylamine → Cyclopropyl-methyl-(3-trimethylsilanylethynyl-phenyl)-amine

HRID 1869956Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869956
Br[C:2]1[CH:3]=[C:4]([N:8]([CH:10]2[CH2:12][CH2:11]2)[CH3:9])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:20][Si:21]([C:24]#[CH:25])([CH3:23])[CH3:22].C(OCC)(=O)C>CCCCCC.[Cu]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>[CH:10]1([N:8]([CH3:9])[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([C:25]#[C:24][Si:21]([CH3:23])([CH3:22])[CH3:20])[CH:3]=2)[CH2:12][CH2:11]1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 21107154(3-Bromo-phenyl)-cyclopropyl-methyl-amine2×

Produkt 1

HCID 57424251Cyclopropyl-methyl-(3-trimethylsilanylethynyl-phenyl)-amineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8058HexaneLösungsmittel

Versuchsvorschrift

Following General Procedure D and using (3-bromo-phenyl)-cyclopropyl-methyl-amine (Intermediate 113, 0.056 g, 0.25 mmol), triethyl amine (3 mL), copper(I)iodide (0.025 g, 0.13 mmol), trimethylsilyl acetylene (2.5 mL, 17.6 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.065 g, 0.09 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 1.5% ethyl acetate in hexane as the eluent, the title compound (0.051 g, 84%) was obtained.

Quellen und Nachweise

ORD-Eintrag
ord-d272361a482247f5a8db477c7cdc7f7d
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638648B2

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