Ethyl isobutyrylacetate → HCID 86682932、化合物

HRID 1497059ノート

反応式

HRID 1497059 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[CH:3]=1.[CH2:18]([O:20][C:21](=[O:28])[CH2:22][C:23](=O)[CH:24]([CH3:26])[CH3:25])[CH3:19]>CCO.C(OCC)(=O)C>[CH2:18]([O:20][C:21]([C:22]1[C:23]([CH:24]([CH3:26])[CH3:25])=[N:8][C:5]2[C:4]([C:9]=1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[O:28])[CH3:19]

参加物

5

反応物 2

HCID 81583Ethyl isobutyrylacetateHCID 86682928HCID 86682928、化合物

生成物 1

HCID 86682932HCID 86682932、化合物収率 23%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4-chloro-2-(2-chloro-phenylethynyl)-phenylamine (prepared as described in example 10 step A, 100 mg, 0.38 mmol) and 4-methyl-3-oxo-pentanoic acid ethyl ester (0.092 ml, 0.57 mmol) in anhydrous EtOH (10 ml), was added p-TsOH—H2O (72.56 mg, 0.38 mmol) and the mixture was refluxed for 72 h. After cooling, the reaction mixture was diluted with ethyl acetate and the organic layer was washed with saturated sodium bicarbonate solution and brine, dried over sodium sulfate, concentrated in vacuo. The crude residue was purified by flash column chromatography (elution with 3% EtOAc in hexane) to give 6-chloro-4-(2-chloro-benzyl)-2-isopropyl-quinoline-3-carboxylic acid ethyl ester (35 mg, 23% yield) as a yellow sticky solid. LC-MS: 402 (M+H)+.

後処理

  1. temperaturethe mixture was refluxed for 72 h
  2. temperatureAfter cooling
  3. washthe organic layer was washed with saturated sodium bicarbonate solution and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash column chromatography (elution with 3% EtOAc in hexane)

出典と根拠

ORDレコード
ord-97ec4c11cd9b466ebc75aa0dc07a5af1
出典データセット
uspto-grants-2015_12
特許番号
US09199938B2

反応ノート

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