Ethyl 2,6-dichloro-4-phenylquinoline-3-carboxylate → HCID 86682959, Verbindung

HRID 1497103Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497103
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]([Cl:22])=[CH:11][CH:10]=2)=[O:5])[CH3:2].[CH:24]1([Mg]Br)[CH2:28][CH2:27][CH2:26][CH2:25]1>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]([Cl:22])=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 1714247Ethyl 2,6-dichloro-4-phenylquinoline-3-carboxylateHCID 178419650HCID 178419650, Verbindung

Produkt 1

HCID 86682959HCID 86682959, VerbindungAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a stirred solution of 2,6-dichloro-4-phenyl-quinoline-3-carboxylic acid ethyl ester (prepared as described in example 11 step B, 100 mg, 0.29 mmol) in 2 ml THF, was added cyclopentyl magnesium bromide (2 M solution in diethyl ether) (0.72 ml, 1.44 mmol) drop wise at 25° C. under nitrogen. The resulting reaction mixture was stirred for 40 min at 50° C. in a microwave. The reaction mixture was then quenched with saturated aqueous NH4Cl solution and extracted with ethyl acetate. The combined organic phases were dried over anhydrous sodium sulfate and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (2% ethyl acetate in hexane) to afford 6-chloro-2-cyclopentyl-4-phenyl-quinoline-3-carboxylic acid ethyl ester (16.5 mg, 15%) as pale yellow sticky solid. LC-MS: 380 (M+H)+.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was then quenched with saturated aqueous NH4Cl solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a crude residue which
  7. customwas purified by flash column chromatography (2% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e7b0f0bf3d0e43e79e3ce58cd4d022dd
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199938B2

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