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Diethyl Ether → 5-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(4-pyridyl)pyrazole

HRID 1274333
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Reaktionsgleichung

Reaktionsgleichung von HRID 1274333
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1I.C(=O)([O-])O.[Na+].[N:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.CCOCC>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:30]1[CH:31]=[CH:32][N:27]=[CH:28][CH:29]=1
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Komponenten

9

Edukt 4

HCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 154620775-Amino-3-cyano-4-iodo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazole

Produkt 1

HCID 98009795-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(4-pyridyl)pyrazole

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 702EthanolLösungsmittel
HCID 962WaterLösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a rapidly stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole (0.25 g) in toluene (2 ml) containing tetrakis(triphenylphosphine)palladium(0) (0.02 g) was added saturated aqueous sodium hydrogen carbonate solution (1 ml) and a solution of 4-pyridylboronic acid (0.153 g) in ethanol (1 ml). The mixture was heated under reflux for 12 hours, then left at room temperature overnight and then poured into ether (25 ml) and water (25 ml). The organic layer was separated, dried (MgSO4) and evaporated. The residue was taken up the minimum amount of ethyl acetate and purified by chromatography on silica gel (20 g) eluted with dichloromethane:methanol (100:1). Combination and evaporation of suitable fractions followed by recrystallisation from ether/hexane dichloromethane gave the title compound as a white solid, m.p. 226-8° C. (decomp.).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. custompurified by chromatography on silica gel (20 g)
  7. washeluted with dichloromethane:methanol (100:1)
  8. customCombination and evaporation of suitable fractions
  9. customfollowed by recrystallisation from ether/hexane dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-e608135b31dd47e8a9166d176a6dbc63
Quelldatensatz
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06156782

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