Tetrahydrofuran → [4-(1-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-6-yl-ethynyl)-2-fluoro-phenyl] acetic acid ethyl ester

HRID 278699

Reaktionsgleichung

Reaktionsgleichung von HRID 278699
COC(=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:13]=[C:14](C3CC3)[C:15]3OC4(CC4)[CH2:18][C:17]([CH3:24])([CH3:23])[C:16]=3[CH:25]=2)=[CH:6][C:5]=1[F:29].[CH2:31]([O:33][C:34](=[O:44])[CH2:35]C1C=CC(I)=CC=1F)[CH3:32].C([N:47]([CH2:50]C)[CH2:48][CH3:49])C.O1CCC[CH2:53]1>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>[CH2:31]([O:33][C:34](=[O:44])[CH2:35][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:25]=[C:16]3[C:15](=[CH:14][CH:13]=2)[N:47]([CH:48]2[CH2:53][CH2:49]2)[CH2:50][CH2:18][C:17]3([CH3:23])[CH3:24])=[CH:6][C:5]=1[F:29])[CH3:32]

Komponenten

9

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 18740710Ethyl 2-fluoro-4-iodophenylacetate2×HCID 695484184-[(8-Cyclopropyl-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzoic acid methyl ester2×

Produkt 1

HCID 69548552[4-(1-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-6-yl-ethynyl)-2-fluoro-phenyl] acetic acid ethyl ester

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 F and using 1-cyclopropyl-6-ethynyl-4,4-dimethyl-1,2,3,4-tetrahydro quinoline (Intermediate 53, 0.11 g, 0.49 mmol), ethyl-2-fluoro-4-iodo-phenyl acetate (Reagent C, 0.11 g, 0.9 mmol), triethyl amine (3 mL), tetrahydrofuran(3 mL), copper(I)iodide(0.06 g, 0.32 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.25 g, 0.36 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent, the title compound was obtained (0.1 g, 51%).

Quellen und Nachweise

ORD-Eintrag
ord-ab92dc87ff0249f88924413257620b54
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06359135B1

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