Tetrahydrofuran → [4-(1-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-6-yl-ethynyl)phenyl]acetic Acid Methyl Ester

HRID 841383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 841383
COC(=O)C1C=CC(C#C[C:12]2[CH:13]=[C:14]([CH:26]3[CH2:28]C3)[C:15]3O[C:19]4(CC4)[CH2:18][C:17]([CH3:24])([CH3:23])[C:16]=3[CH:25]=2)=CC=1F.[CH3:31][O:32][C:33](=[O:42])[CH2:34][C:35]1[CH:40]=[CH:39][C:38](I)=[CH:37][CH:36]=1.C([N:45]([CH2:48][CH3:49])CC)C.O1CCC[CH2:51]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>[CH3:31][O:32][C:33](=[O:42])[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:28]#[C:26][C:14]2[CH:15]=[C:16]3[C:25](=[CH:12][CH:13]=2)[N:45]([CH:48]2[CH2:49][CH2:51]2)[CH2:19][CH2:18][C:17]3([CH3:23])[CH3:24])=[CH:37][CH:36]=1

Komponenten

9

Edukt 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10378700Methyl 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 10270709[4-(1-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-6-yl-ethynyl)phenyl]acetic Acid Methyl 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, 0.05 g, 0.22 mmol), methyl-4-iodo-phenyl acetate (Reagent B, 0.055 g, 0.2 mmol), triethyl amine (5 mL), tetrahydrofuran, copper(I)iodide (0.025 g, 0.13 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.75 g, 0.11 mmol) followed preparative normal phase HPLC using 10% ethyl acetate in hexane as the mobile phase, the title compound was obtained (0.089 g, 100%).

Quellen und Nachweise

ORD-Eintrag
ord-311e01b86f3042afb9fb2c46c0a42c4c
Quelldatensatz
uspto-grants-2002_04
Patentnummer
US06369225B1

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