Tetrahydrofuran → HCID 69076270, Verbindung

HRID 2377442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2377442
[CH:1]([O:4][C:5](=[O:19])[C:6]1[CH:11]=[CH:10][C:9](Br)=[CH:8][C:7]=1[CH2:13][N:14]([CH:16]1[CH2:18][CH2:17]1)[CH3:15])([CH3:3])[CH3:2].C(N(CC)CC)C.O1CCCC1.[CH3:32][Si:33]([C:36]#[CH:37])([CH3:35])[CH3:34]>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.C(OCC)(=O)C>[CH:1]([O:4][C:5](=[O:19])[C:6]1[CH:11]=[CH:10][C:9]([C:37]#[C:36][Si:33]([CH3:35])([CH3:34])[CH3:32])=[CH:8][C:7]=1[CH2:13][N:14]([CH:16]1[CH2:18][CH2:17]1)[CH3:15])([CH3:3])[CH3:2]

Komponenten

9

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 574242544-Bromo-2-[(cyclopropyl-methylamino)-methyl]-benzoic acid isopropyl ester2×

Produkt 1

HCID 69076270HCID 69076270, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Following General Procedure D and using 4-bromo-2-[(cyclopropyl-methyl-amino)-methyl]-benzoic acid isopropyl ester (Intermediate 120, 1.23 g, 3.68 mmol), triethyl amine (10 mL), tetrahydrofuran (5 mL), copper(I)iodide (0.21 g, 1.1 mmol), trimethylsilyl acetylene (2.1 mL, 14.7 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.77 g, 1.1 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 7% ethyl acetate in hexane as the eluent, the title compound was obtained as an oil (1.2 g, ˜100%).

Quellen und Nachweise

ORD-Eintrag
ord-0d2242810c1b4dbd90aca07de4b43012
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468391B2

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