Ethyl 3-cyclopropyl-3-oxopropanoate → HCID 86682929, 화합물

HRID 1497051노트

반응식

HRID 1497051 반응식
[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]

참가 물질

5

반응물 3

HCID 262979Ethyl 3-cyclopropyl-3-oxopropanoateHCID 521998p-Toluenesulfonic acid monohydrateHCID 86682928HCID 86682928, 화합물

생성물 1

HCID 86682929HCID 86682929, 화합물수율 22%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-6fad11c4740a4507b2040faccafb0658
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199938B2

반응 노트

불러오는 중…