Ammonia → 4-[(4-chlorobenzyl)oxy]-1-(2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-one

HRID 1497357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497357
Br[C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[C:5]([CH3:12])[N:6]([CH3:11])[N:7]=2)[CH:3]=1.[Cl:13][C:14]1[CH:28]=[CH:27][C:17]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][NH:23][C:22](=[O:26])[CH:21]=2)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CNCCNC.N>CS(C)=O.[Cu]I>[Cl:13][C:14]1[CH:28]=[CH:27][C:17]([CH2:18][O:19][C:20]2[CH:25]=[CH:24][N:23]([C:2]3[CH:10]=[CH:9][C:8]4[C:4](=[C:5]([CH3:12])[N:6]([CH3:11])[N:7]=4)[CH:3]=3)[C:22](=[O:26])[CH:21]=2)=[CH:16][CH:15]=1

Komponenten

8

Edukt 5

HCID 222AmmoniaHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 114995675-bromo-2,3-dimethyl-2H-indazoleHCID 574978644-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-one

Produkt 1

HCID 865829744-[(4-chlorobenzyl)oxy]-1-(2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-oneAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A suspension of 5-bromo-2,3-dimethyl-2H-indazole (287 mg), 4-[(4-chlorobenzyl)oxy]pyridin-2(1H)-one (300 mg), potassium carbonate (528 m g), copper(I) iodide (242 mg) and N,N′-dimethylethylenediamine (112 mg) in DMSO (10 ml) was stirred at 150° C. for 3 hr. The reaction mixture was cooled to room temperature, added to 28% aqueous ammonia, and extracted with a 1:1 mixed solvent of ethyl acetate and tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (150 mg).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with a 1:1 mixed solvent of ethyl acetate and tetrahydrofuran
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-4be5abcf7a1e46e5822172de251cdf8e
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199963B2

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