Cesium carbonate → 4-tert-butyl-N-[5-chloro-2-(4-nitro-pyrazol-1-yl)-pyridin-3-yl]-benzenesulfonamide

HRID 75992

Reaktionsgleichung

Reaktionsgleichung von HRID 75992
Br[C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([Cl:22])=[CH:4][N:3]=1.[N+:23]([C:26]1[CH:27]=[N:28][NH:29][CH:30]=1)([O-:25])=[O:24].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C(=O)C.[Cu](I)I.O.C(OCC)(=O)C>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([S:9]([NH:8][C:7]2[C:2]([N:28]3[CH:27]=[C:26]([N+:23]([O-:25])=[O:24])[CH:30]=[N:29]3)=[N:3][CH:4]=[C:5]([Cl:22])[CH:6]=2)(=[O:11])=[O:10])=[CH:13][CH:14]=1)([CH3:21])([CH3:20])[CH3:19]

Komponenten

9

Edukt 4

HCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 57942597N-(2-bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-benzenesulfonamide

Produkt 1

HCID 684640854-tert-butyl-N-[5-chloro-2-(4-nitro-pyrazol-1-yl)-pyridin-3-yl]-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 83717Copper iodideKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A solution of N-(2-bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-benzene sulfonamide (534 mg, 1.32 mmol), 4-nitropyrazole (224 mg, 1.98 mmol), trans-N,N′-dimethyl-cyclohexane-1,2-diamine (42 μL, 0.264 mmol), copper iodide (51 mg, 0.264 mmol), and cesium carbonate (903 mg, 2.77 mmol) in 5 mL of N,N-dimethylacetamide was heated at 130° C. for 2 hours. Ethyl acetate and water were added and the layers were separated. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude reside was subsequently purified by flash column chromatography (0-100% ethyl acetate in hexanes) to afford 4-tert-butyl-N-[5-chloro-2-(4-nitro-pyrazol-1-yl)-pyridin-3-yl]-benzenesulfonamide as a white solid.

Aufarbeitung

  1. customthe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude reside was subsequently purified by flash column chromatography (0-100% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f9f0f6399497473a809f2b5cef77dd9d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835468B2

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