Ethyl Acetate → HCID 57808267, Verbindung

HRID 730317

Reaktionsgleichung

Reaktionsgleichung von HRID 730317
[N:1]([C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[C:7]([OH:14])[CH:8]=[CH:9][CH:10]=2)[N:5]=1)=[N+]=[N-].Cl[C:16]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[CH:19]=[CH:18][N:17]=1.[H-].[Na+].CCOC(C)=O>CN(C=O)C.[Cl-].[Na+].O>[F:31][C:28]([F:29])([F:30])[C:25]1[CH:24]=[CH:23][C:22]([C:20]2[CH:21]=[CH:16][N:17]=[C:18]([O:14][C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:6]=3[N:5]=[C:4]([NH2:1])[CH:13]=[CH:12]4)[CH:19]=2)=[CH:27][CH:26]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 21865093HCID 21865093, VerbindungHCID 288758632-Chloro-4-(4-trifluoromethylphenyl)pyridine

Produkt 1

HCID 57808267HCID 57808267, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of 2-azido-quinolin-8-ol (0.28 g, 1.5 mmol), 2-chloro-4-(4-trifluoromethyl-phenyl)-pyridine (Example 410 (c), 0.26 g, 1 mmol), and sodium hydride (64 mg, 1.6 mmol) in DMF (2 mL) was heated in a 180° C. oil bath for 48 h. The reaction mixture was then transferred to a 5-mL tube, and irradiated in the Microwave Smith Synthesizer at 250° C. for 10 min. EtOAc and brine were added, and the aqueous layer was extracted with EtOAc. Combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The compound was purified on a Biotage 40S column (98:2 dichloromethane:MeOH) followed by recrystallization from EtOAc/hexanes to give the title compound as a light-yellow shiny crystal. MS (ESI, pos. ion) m/z: 382 (M+1). Mp: 196.5-199.5° C. Anal. Calcd for C21H14F3N3O: C, 66.14; H, 3.70; N, 11.02. Found: C, 66.18; H, 3.69; N, 11.08.

Aufarbeitung

  1. customThe reaction mixture was then transferred to a 5-mL tube
  2. customirradiated in the Microwave Smith Synthesizer at 250° C. for 10 min
  3. extractionthe aqueous layer was extracted with EtOAc
  4. dry with materialCombined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe compound was purified on a Biotage 40S column (98:2 dichloromethane:MeOH)
  8. customfollowed by recrystallization from EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f53bcbb165f84166a16279384091df26
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582657B2

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