Tetrahydrofuran → HCID 69076270, Verbindung

HRID 1869962Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869962
[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-methylamino)-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-701661fb99ab475bab0148206c0a9236
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638648B2

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