Triethylamine → (E)-3-(4-{5-[(Cyclopropyl-methyl-amino)-methyl]-2-methyl-phenylethynyl}-phenyl)-acrylic acid ethyl ester

HRID 1869942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869942
[CH:1]1([N:4]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([C:14]#[CH:15])[CH:8]=2)[CH3:5])[CH2:3][CH2:2]1.[CH2:16]([O:18][C:19](=[O:48])/[C:20](/C)=[CH:21]/[C:22]1[CH:27]=[CH:26][C:25](C#CC2C=C(C3CC3)C3OC4(CC4)C(C)=C(C)C=3C=2)=[CH:24][CH:23]=1)[CH3:17].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>[CH2:16]([O:18][C:19](=[O:48])/[CH:20]=[CH:21]/[C:22]1[CH:27]=[CH:26][C:25]([C:15]#[C:14][C:9]2[CH:8]=[C:7]([CH2:6][N:4]([CH:1]3[CH2:3][CH2:2]3)[CH3:5])[CH:12]=[CH:11][C:10]=2[CH3:13])=[CH:24][CH:23]=1)[CH3:17]

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 21107259Cyclopropyl-(3-ethynyl-4-methylbenzyl)-methyl-amine2×HCID 69069630(E)-3-{4-[8-Cyclopropyl-3,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl]ethynyl-phenyl}-2-methyl-acrylic acid ethyl ester2×

Produkt 1

HCID 57462494(E)-3-(4-{5-[(Cyclopropyl-methyl-amino)-methyl]-2-methyl-phenylethynyl}-phenyl)-acrylic 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 cyclopropyl-(3-ethynyl-4-methylbenzyl)-methyl-amine (Intermediate 99, 0.095 g, 0.48 mmol), ethyl-4-iodo-cinnamate (Reagent 3, 0.144 g, 0.47 mmol), triethyl amine (13 mL), copper(I)iodide (0.019 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.071 g, 0.1 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 5-20% ethyl acetate in hexane as the eluent, the title compound was obtained (0.14 g, 82%).

Quellen und Nachweise

ORD-Eintrag
ord-511be8cf1de84d19b9024ddb8dc1bb6f
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638648B2

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