Cesium carbonate → HCID 59316726, compound

HRID 2189804Notes

Reaction equation

HRID 2189804 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:18][CH2:19][C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH2:18][CH2:19][C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 14536789Ethyl 4-bromo-2,2-dimethylbutanoateHCID 223525484-bromo-1H-indazole

Product 1

HCID 59316726HCID 59316726, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-bromo-1H-indazole (commercially available from Insight Chemical Solutions Ltd., 826 mg, 4.19 mmol) in DMF (10 ml) at room temperature were added Cs2CO3 (1.37 g, 4.19 mmol) and ethyl 4-bromo-2,2-dimethylbutanoate (D99) (1.40 g, 6.29 mmol) and the resulting mixture was stirred at 80° C. for 24 h then cooled to room temperature and diluted with AcOEt. The organic phase was washed with water, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel [15-25% EtOAc/cyclohexane] gave the title compound (600 mg, 40%) as orange oil. MS (ES) C15H1981BrN2O2 requires 340, found 341 [M+H]+

Workup

  1. temperaturethen cooled to room temperature
  2. washThe organic phase was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification of the residue by flash chromatography on silica gel [15-25% EtOAc/cyclohexane]

Sources & evidence

ORD record
ord-a83195d925484526a9f2ec533d0bafb5
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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