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

HRID 2089214Notes

Reaction equation

HRID 2089214 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-76743a174e1549b3975a3527bff2e547
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

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