Ethyl pyridine-4-acetate → 3-(4-Chloro-phenyl)-3-[3-(6-isopropyl-quinolin-8-yl)-phenyl]-2-pyridin-4-yl-propionic acid ethyl ester

HRID 896683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 896683
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:3][CH:2]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Cl[CH:24]([C:44]1[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][CH:45]=1)[C:25]1[CH:26]=[C:27]([C:31]2[CH:32]=[C:33]([CH:41]([CH3:43])[CH3:42])[CH:34]=[C:35]3[C:40]=2[N:39]=[CH:38][CH:37]=[CH:36]3)[CH:28]=[CH:29][CH:30]=1>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C.[Cl-].[NH4+].C(OCC)(=O)C>[CH2:11]([O:10][C:8](=[O:9])[CH:7]([C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)[CH:24]([C:44]1[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][CH:45]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]2[CH:32]=[C:33]([CH:41]([CH3:43])[CH3:42])[CH:34]=[C:35]3[C:40]=2[N:39]=[CH:38][CH:37]=[CH:36]3)[CH:26]=1)[CH3:12]

Komponenten

7

Edukt 3

HCID 736321Ethyl pyridine-4-acetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 223501108-{3-[Chloro-(4-chloro-phenyl)-methyl]-phenyl}-6-isopropyl-quinoline

Produkt 1

HCID 208149663-(4-Chloro-phenyl)-3-[3-(6-isopropyl-quinolin-8-yl)-phenyl]-2-pyridin-4-yl-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8857Ethyl AcetateLösungsmittelHCID 25517Ammonium ChlorideLösungsmittelHCID 86583969tetrahydrofuran HMPALösungsmittel

Reaktionsbedingungen

Temperatur
21 °C

Versuchsvorschrift

To a solution of ethyl 4-pyridinylacetate (1.28 g, 7.74 mmol) in THF/HMPA (3:1, 5 mL) at −10° C. was added NaHMDS (1M, 7.8 mL, 7.8 mmol) dropwise. After 60 min., the crude chloride from Step 2 above was added and the resulting reaction mixture was stirred for 18 h at 21° C., and then diluted with a saturated ammonium chloride solution and ethyl acetate. The organic extracts were washed (H2O, brine), dried (MgSO4), filtered and concentrated.

Aufarbeitung

  1. customthe resulting reaction mixture
  2. washThe organic extracts were washed (H2O, brine)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d6d57069dc714e23b79b60f542161d26
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919353B2

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