Triethylamine → 2-[3-(3-Fluoro-4-methoxycarbonylmethyl-phenylethynyl)-phenyl]-2-methyl-propionic acid ethyl ester

HRID 1765847Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1765847
[CH2:1]([O:3][C:4](=[O:16])[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[CH:15])[CH:9]=1)([CH3:7])[CH3:6])[CH3:2].[CH3:17][O:18][C:19](=[O:29])[CH2:20][C:21]1[CH:26]=[CH:25][C:24](I)=[CH:23][C:22]=1[F:28].C(N(CC)CC)C.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>[CH2:1]([O:3][C:4](=[O:16])[C:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]#[C:15][C:24]2[CH:25]=[CH:26][C:21]([CH2:20][C:19]([O:18][CH3:17])=[O:29])=[C:22]([F:28])[CH:23]=2)[CH:9]=1)([CH3:6])[CH3:7])[CH3:2]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 187102252-Fluoro-4-iodo phenyl acetic acid methyl esterHCID 574242582-(3-Ethynyl-phenyl)-2-methyl-propionic acid ethyl ester2×

Produkt 1

HCID 690758222-[3-(3-Fluoro-4-methoxycarbonylmethyl-phenylethynyl)-phenyl]-2-methyl-propionic acid ethyl ester

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 B and using 2-(3-ethynyl-phenyl)-2-methyl-propionic acid ethyl ester (Intermediate 132, 0.10 g, 0.46 mmol), 2-fluoro-4-iodo phenyl acetic acid methyl ester (0.136 g, 0.46 mmol), triethyl amine (8 mL), copper(I)iodide (0.01 g, 0.05 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.035 g, 0.05 mmol) followed by flash column chromatography over silica gel (230–400 mesh) using 10–15% ethyl acetate in hexane as the eluent, the title compound was obtained as an oil (0.15 g, 85%).

Quellen und Nachweise

ORD-Eintrag
ord-ca937e4e6d814638b83bf69e1d54b665
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07226951B2

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