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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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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2364212
[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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Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11
1,2-Dichloroethane
Lösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0aee52c5584a4fac922b3221e8569882
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08691991B2

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