tert-Butyl isocyanate → 3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-5-trifluoromethyl-indazole-1-carboxylic acid tert-butyl amide

HRID 2089214Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2089214
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22].[C:25]([N:29]=[C:30]=[O:31])([CH3:28])([CH3:27])[CH3:26]>CN(C=O)C>[C:25]([NH:29][C:30]([N:8]1[C:9]2[C:5](=[CH:4][C:3]([C:2]([F:23])([F:1])[F:24])=[CH:11][CH:10]=2)[C:6]([N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])=[N:7]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]

Komponenten

4

Edukt 2

HCID 62412tert-Butyl isocyanateHCID 585488622-(5-Trifluoromethyl-1H-indazol-3-yl)-isoindole-1,3-dione

Produkt 1

HCID 585487433-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-5-trifluoromethyl-indazole-1-carboxylic acid tert-butyl amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(5-Trifluoromethyl-1H-indazol-3-yl)-isoindole-1,3-dione (1.56 g, 4.71 mmol) in DMF (5 mL) was treated with t-butyl-isocyanate (513 mg, 5.18 mmol) at room temperature overnight. The reaction was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude material. Purification by silica gel column (hexanes:ethyl acetate 2:1) afforded the title compound as colorless solid.

Aufarbeitung

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude material
  7. customPurification by silica gel column (hexanes:ethyl acetate 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-76743a174e1549b3975a3527bff2e547
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436023B2

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