Sodium bis(trimethylsilyl)amide → 4-{1-[(2E)-but-2-en-1-yloxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline

HRID 25785

Reaktionsgleichung

Reaktionsgleichung von HRID 25785
C(OC(N1C2C(=CC(C3C=CC=CC=3OC)=CC=2)C(C(O)C)=CC1(C)C)=O)(C)(C)C.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:39]1[CH:40]=[C:41]2[C:46](=[CH:47][CH:48]=1)[NH:45][C:44]([CH3:50])([CH3:49])[CH:43]=[C:42]2[CH:51]([O:53][CH2:54][CH2:55][CH2:56][C:57]1C=CC=CC=1)[CH3:52].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CS(C)=O.C1COCC1.BrCCCC1C=CC=CC=1>[CH2:54]([O:53][CH:51]([C:42]1[C:41]2[C:46](=[CH:47][CH:48]=[C:39]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[O:32][CH3:31])[CH:40]=2)[NH:45][C:44]([CH3:50])([CH3:49])[CH:43]=1)[CH3:52])/[CH:55]=[CH:56]/[CH3:57]

Komponenten

6

Edukt 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 691540386-(2-Methoxyphenyl)-2,2-dimethyl-4-[1-(3-phenylpropoxy)ethyl]-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 103166704-{1-[(2E)-but-2-en-1-yloxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolineAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 12503(3-Bromopropyl)benzeneLösungsmittel

Versuchsvorschrift

6-(2-Methoxyphenyl)-2,2-dimethyl-4-[1-(3-phenylpropoxy)ethyl]-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester (116 mg) in 2 mL of DMSO was treated with 334 μL of 1 M solution of sodium bis(trimethylsilyl)amide in THF and 52 μL of 1-bromo-3-phenylpropane to give the alkylated product, which was then deprotected (as above) to yield 31 mg of the title compound as an oil.

Aufarbeitung

  1. customto give the alkylated product, which

Quellen und Nachweise

ORD-Eintrag
ord-84a4bd1588cb4f438526b2da20c9be26
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858627B2

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