Ethyl 3-cyclopropyl-3-oxopropanoate → HCID 86682929、化合物

HRID 1497051ノート

反応式

HRID 1497051 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.[CH:18]1([C:21](=O)[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:20][CH2:19]1.CC1C=CC(S(O)(=O)=O)=CC=1.O>CCO>[CH2:26]([O:25][C:23]([C:22]1[C:21]([CH:18]2[CH2:20][CH2:19]2)=[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:24])[CH3:27]

参加物

5

反応物 3

HCID 262979Ethyl 3-cyclopropyl-3-oxopropanoateHCID 521998p-Toluenesulfonic acid monohydrateHCID 86682928HCID 86682928、化合物

生成物 1

HCID 86682929HCID 86682929、化合物収率 22%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 4-chloro-2-(2-chloro-phenylethynyl)-phenylamine (100 mg, 0.38 mmol, 1 eq) and ethyl 3-cyclopropyl-3-oxopropanoate (89.4 mg, 0.57 mmol, 1.5 eq) in anhydrous EtOH (5 ml), was added p-TsOH.H2O (72.6 mg, 0.38 mmol, 1 eq) and the mixture was refluxed for 16 h. After cooling, the reaction mixture was concentrated in vacuo and then diluted with ethyl acetate. The mixture was washed with saturated sodium bicarbonate solution, brine, dried over sodium sulfate and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (elution with 3% ethyl acetate in hexane) to give 6-chloro-4-(2-chloro-benzyl)-2-cyclopropyl-quinoline-3-carboxylic acid ethyl ester (33 mg, 22%) as a pale yellow solid. MS (ESI): 400.0 (M+H)+.

後処理

  1. temperaturethe mixture was refluxed for 16 h
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. additiondiluted with ethyl acetate
  5. washThe mixture was washed with saturated sodium bicarbonate solution, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give a crude residue which
  9. customwas purified by flash column chromatography (elution with 3% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-6fad11c4740a4507b2040faccafb0658
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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