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Ethyl 3-chloro-3-oxopropionate → Ethyl 3-[(3-ethoxy-3-oxopropanoyl)(4-fluorophenyl)amino]-5-(4-fluorobenzyl)pyridine-2-carboxylate

HRID 2364212
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HRID 2364212 반응식
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7]2[CH:8]=[C:9]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:11][CH:12]=2)=[CH:4][CH:3]=1.Cl[C:29](=[O:36])[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].CO.ClCCl>ClCCCl>[CH2:34]([O:33][C:31](=[O:32])[CH2:30][C:29]([N:18]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:9]1[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:11][CH:12]=[C:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:27][CH:26]=2)[CH:8]=1)=[O:36])[CH3:35]
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참가 물질

5

반응물 3

HCID 118931Ethyl 3-chloro-3-oxopropionateHCID 21226129Dichloromethane methanolHCID 69482193Ethyl 5-(4-fluorobenzyl)-3-[(4-fluorophenyl)amino]pyridine-2-carboxylate

생성물 1

HCID 69481480Ethyl 3-[(3-ethoxy-3-oxopropanoyl)(4-fluorophenyl)amino]-5-(4-fluorobenzyl)pyridine-2-carboxylate수율 80%

시약·촉매·용매 1

HCID 11
1,2-Dichloroethane
용매

실험 절차

To a solution of ethyl 5-(4-fluorobenzyl)-3-[(4-fluorophenyl)amino]pyridine-2-carboxylate (456 mg, 1.24 mmol) in 1,2-dichloroethane was added ethyl 3-chloro-3-oxopropanoate (0.18 mL, 2.36 mmol) and the resulting yellow solution was refluxed for 1 hour or until determined complete by TLC (5% methanol/dichloromethane). The mixture was cooled to ambient temperature, quenched with water and extracted with dichloromethane. The organics were washed with saturated aqueous sodium bicarbonate, brine, and dried over sodium sulfate to yield ethyl 3-[[3-(ethyloxy)-3-oxopropanoyl](4-fluorophenyl)amino]-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (477 mg, 80% yield) as mixture of rotamers. The yellow oil can be carried on without further purification or purified by silica gel chromatography (0-12% methanol/dichloromethane gradient elution). Spectral data was consistent with the expected product as mixture of rotamers. MS m/z 505 (M+23).

후처리

  1. temperaturethe resulting yellow solution was refluxed for 1 hour
  2. customquenched with water
  3. extractionextracted with dichloromethane
  4. washThe organics were washed with saturated aqueous sodium bicarbonate, brine
  5. dry with materialdried over sodium sulfate

출처 및 근거

ORD 기록
ord-0aee52c5584a4fac922b3221e8569882
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08691991B2

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