Sodium bis(trimethylsilyl)amide → 4-{1-[2-(2-bromophenyl)ethoxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

HRID 25793Notes

Reaction equation

HRID 25793 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][OH:6].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:21]([O:25][C:26]([N:28]1[C:37]2[C:32](=[CH:33][C:34]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[O:44][CH3:45])=[CH:35][CH:36]=2)[C:31]([CH:46](OS(C)(=O)=O)[CH3:47])=[CH:30][C:29]1([CH3:54])[CH3:53])=[O:27])([CH3:24])([CH3:23])[CH3:22]>CS(C)=O>[C:21]([O:25][C:26]([N:28]1[C:37]2[C:32](=[CH:33][C:34]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[O:44][CH3:45])=[CH:35][CH:36]=2)[C:31]([CH:46]([O:6][CH2:5][CH2:4][C:3]2[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=2[Br:1])[CH3:47])=[CH:30][C:29]1([CH3:53])[CH3:54])=[O:27])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 27340892-(2-Bromophenyl)ethan-1-olHCID 207603354-(1-methanesulfonyloxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

Product 1

HCID 691528124-{1-[2-(2-bromophenyl)ethoxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A mixture of 0.037 mL of 2-bromophenethyl alcohol and 1 mL of DMSO was treated with 0.277 mL of 1.0 M sodium bis(trimethylsilyl)amide, then 86 mg of 4-(1-methanesulfonyloxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester in 1 mL DMSO was added at room temperature. The reaction mixture was allowed to stir at room temperature overnight. TLC showed starting material was consumed. The reaction was quenched with water and the product was extracted with EtOAc three times. The organic layers were combined, washed sequentially with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution, water, and brine, dried over magnesium sulfate, and the solvent evaporated in vacuo. The residue was purified by flash chromatography to yield 37 mg of 4-{1-[2-(2-bromophenyl)ethoxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester as an oil.

Workup

  1. customwas consumed
  2. customThe reaction was quenched with water
  3. extractionthe product was extracted with EtOAc three times
  4. washwashed sequentially with saturated aqueous ammonium chloride solution, saturated aqueous sodium bicarbonate solution, water, and brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent evaporated in vacuo
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e63432d334d242ebae9c7ada2d5c089d
Source dataset
uspto-grants-2005_02
Patent number
US06858627B2

Reaction notes

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