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

HRID 25791

Reaction equation

HRID 25791 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][CH2:55][C:56]1C=CC=C[CH:57]=1)[CH3:52].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1.C(Br)CC1C=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]

Participants

5

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 691525016-(2-Methoxyphenyl)-2,2-dimethyl-4-(1-phenethyloxyethyl)-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 140.4%

Reagents, catalysts & solvents 2

HCID 7666Phenethyl bromideSolventHCID 8028TetrahydrofuranSolvent

Procedure

6-(2-Methoxyphenyl)-2,2-dimethyl-4-(1-phenethyloxyethyl)-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester (100 mg) was treated with 360 μL of 1 M solution of sodium bis(trimethylsilyl)amide in THF and 45 μL of phenethyl bromide to give the alkylated product, which was deprotected to yield 62 mg of the title compound as an oil.

Workup

  1. customto give the alkylated product, which

Sources & evidence

ORD record
ord-f7d5dd04ee0f424a9cdb3a8acaf6d5c2
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Linked notes

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