Triethylamine → Methyl{4-[4-(1-methoxycyclopropyl)-phenylethynyl]-phenyl}-acetate

HRID 24140

Reaktionsgleichung

Reaktionsgleichung von HRID 24140
[CH2:1]([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12]C2C=C3C(=CC=2)N(C2CC2)CCC3(C)C)=[CH:7][CH:6]=1)C.[CH3:29][O:30][C:31](=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][C:36](I)=[CH:35][CH:34]=1.[CH2:41](N(CC)CC)[CH3:42]>[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>[CH3:29][O:30][C:31](=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:12]#[C:11][C:8]2[CH:7]=[CH:6][C:5]([C:4]3([O:3][CH3:1])[CH2:42][CH2:41]3)=[CH:10][CH:9]=2)=[CH:35][CH:34]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 10378700Methyl 4-Iodophenylacetate2×HCID 695488784-(1-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-6-yl-ethynyl)-benzoic acid ethyl ester2×

Produkt 1

HCID 86585921Methyl{4-[4-(1-methoxycyclopropyl)-phenylethynyl]-phenyl}-acetateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysator

Versuchsvorschrift

Using General Procedure F; 1-ethynyl-4-(1-methoxycyclopropyl)-benzene (Intermediate 61, 120.0 mg, 0.56 mmol) and methyl-(4-iodophenyl)-acetate (Reagent B, 154.0 mg, 0.56 mmol) in triethyl amine (6 mL) was treated with copper(I)iodide (35.0 mg, 0.19 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (130 mg, 0.19 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-8% EtOAc—hexanes) afforded 140.0 mg (78%) of the title compound as an orange solid.

Aufarbeitung

  1. customsparged with argon for 5 minutes

Quellen und Nachweise

ORD-Eintrag
ord-e5c46863350e440095e86e1636b8d707
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855512B2

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