Acetic Acid → 5-(6-Chloroimidazo[1,2-a]pyrazin-2-yl)-2-(trifluoromethyl)aniline

HRID 539795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 539795
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[C:13]([N+:21]([O-])=O)[CH:12]=3)[N:10]=2)[CH:7]=1.CC(O)=O>[Fe].C(O)C.O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:20])[F:19])=[C:13]([CH:12]=3)[NH2:21])[N:10]=2)[CH:7]=1

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 575162776-Chloro-2-[3-nitro-4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine

Produkt 1

HCID 575162785-(6-Chloroimidazo[1,2-a]pyrazin-2-yl)-2-(trifluoromethyl)anilineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 19096565Water ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Iron (0.726 g) is added to a mixture of 6-chloro-2-[3-nitro-4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrazine (0.891 g), HOAc (1.19 mL), and EtOH—H2O (10 mL, 4:1). The mixture is stirred at 80° C. for 2 hours, cooled, concentrated and taken up into sat. aqueous NaHCO3 and extracted with EtOAc and CH2Cl2. Organic layer is dried and concentrated to give the title compound (813 mg), which is used without further purification. LCMS m/z=313.4 [M+H]+, tR=2.29 min.

Aufarbeitung

  1. temperaturecooled
  2. concentrationconcentrated
  3. extractionextracted with EtOAc and CH2Cl2
  4. customOrganic layer is dried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4fdee28838ad46b696f951ad01edb476
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871767B2

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