Ethyl Acetate → 2-Chloro-8-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-quinoline

HRID 857608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857608
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[CH:4][N:3]=1.[Cl:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[C:22]([OH:29])[CH:23]=[CH:24][CH:25]=2)[N:20]=1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C.[Cl-].[Na+].O>[Cl:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[C:22]([O:29][C:2]3[CH:7]=[C:6]([C:8]4[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=4)[N:5]=[CH:4][N:3]=3)[CH:23]=[CH:24][CH:25]=2)[N:20]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2748782-Chloroquinolin-8-olHCID 167478374-Chloro-6-(4-(trifluoromethyl)phenyl)pyrimidine

Produkt 1

HCID 100240132-Chloro-8-[6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yloxy]-quinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

solution of 4-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidine, (Example 2(a), Method A), (259 mg, 1 mmol) and 2-chloro-quinolin-8-ol (Example 2(a), Method B), (180 mg, 1 mmol) in 2 mL of DMF was added potassium carbonate (276 mg, 2 mmol). The reaction was stirred in a 90° C. oil bath for 2 h. EtOAc and brine were added, and the aqueous layer was extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuum. Purification by flash chromatography by silica gel chromatography 1:4 of EtOAc/hexanes as eluent gave the title compound as a white solid. MS (ESI, pos. ion) m/z: 402 (M+1). Mp: 171.5–173.0° C. Anal. Calcd for C20H11ClF3N3O: C, 59.79; H, 2.76; N, 10.46. Found: C, 60.01; H, 2.80; N, 10.50.

Aufarbeitung

  1. extractionthe aqueous layer was extracted with EtOAc
  2. washThe combined EtOAc layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customPurification by flash chromatography by silica gel chromatography 1:4 of EtOAc/hexanes as eluent

Quellen und Nachweise

ORD-Eintrag
ord-da8d2a4ed3cb4168bcdb8358902bde96
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144888B2

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