Réaction #54065

ord-ce9a7ee077a34850b30661c174215de3

Équation de réaction

COc1ccccc1-c1ccc2c(c1)C(C(C)O)=CC(C)(C)N2C(=O)OC(C)(C)C.COc1ccccc1-c1ccc2c(c1)C(C(C)OCCC1CCCCC1)=CC(C)(C)N2
4-[1-(2-Cyclohexylethoxy)ethyl]-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester
C[Si](C)(C)[N-][Si](C)(C)C.[Na+]
sodium bis(trimethylsilyl)amide
BrCCC1CCCCC1
2-cyclohexylethyl bromide
→
C/C=C/COC(C)C1=CC(C)(C)Nc2ccc(-c3ccccc3OC)cc21
title compound
Rendement 101.0%
C/C=C/COC(C)C1=CC(C)(C)Nc2ccc(-c3ccccc3OC)cc21
4-{1-[((E)-but-2-enyl)oxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline
Rendement 101.0%

Réactifs

—
solution
COc1ccccc1-c1ccc2c(c1)C(C(C)O)=CC(C)(C)N2C(=O)OC(C)(C)C.COc1ccccc1-c1ccc2c(c1)C(C(C)OCCC1CCCCC1)=CC(C)(C)N2
4-[1-(2-Cyclohexylethoxy)ethyl]-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester
C[Si](C)(C)[N-][Si](C)(C)C.[Na+]
sodium bis(trimethylsilyl)amide
BrCCC1CCCCC1
2-cyclohexylethyl bromide

Réactifs

Aucun

Solvants

C1CCOC1
THF

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autreto give the alkylated product, which

Mode opératoire

4-[1-(2-Cyclohexylethoxy)ethyl]-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester (70 mg) was treated with 255 μL of 1 M solution of sodium bis(trimethylsilyl)amide in THF and 49 mg of 2-cyclohexylethyl bromide to give the alkylated product, which was deprotected to yield 31 mg of title compound as an oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US06858627B2uspto-grants-2005_02