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 25793

反応式

HRID 25793 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e63432d334d242ebae9c7ada2d5c089d
出典データセット
uspto-grants-2005_02
特許番号
US06858627B2

関連ノート

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