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

HRID 25790

Reaction equation

HRID 25790 reaction equation
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][CH:55]=[C:56](C)[CH3:57])[CH3:52].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1.BrCC=C(C)C>[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]

Participants

5

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 691537276-(2-Methoxyphenyl)-2,2-dimethyl-4-[1-(3-methylbut-2-enyloxy)ethyl]-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

Product 1

HCID 103166704-{1-[(2E)-but-2-en-1-yloxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinolineYield 32.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 700922-Butene, 1-bromo-3-methyl-Solvent

Procedure

6-(2-Methoxyphenyl)-2,2-dimethyl-4-[1-(3-methylbut-2-enyloxy)ethyl]-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester (96 mg) was treated with 450 μL of 1 M solution of sodium bis(trimethylsilyl)amide in THF and 50 μL of 4-bromo-2-methyl-2-butene to give the alkylated product, which was deprotected to yield 14.5 mg of the title compound as an oil.

Workup

  1. customto give the alkylated product, which

Sources & evidence

ORD record
ord-d5f249d5ca93471aaf3c153cf810d56a
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Linked notes

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