Cesium carbonate → Ethyl 3-(4-cyano-1H-indazol-1-yl)-2,2-dimethylpropanoate

HRID 2189794Notes

Reaction equation

HRID 2189794 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]#[N:11])[C:4]=2[CH:3]=[N:2]1.Br[CH2:13][C:14]([CH3:21])([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[C:10]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[N:2][N:1]2[CH2:13][C:14]([CH3:21])([CH3:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:11]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 12373576Ethyl 3-bromo-2,2-dimethylpropanoateHCID 247293471H-Indazole-4-carbonitrile

Product 1

HCID 59316699Ethyl 3-(4-cyano-1H-indazol-1-yl)-2,2-dimethylpropanoateYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1H-Indazole-4-carbonitrile (commercially available from Insight Chemical Solutions Ltd.) (500 mg, 3.49 mmol), ethyl 3-bromo-2,2-dimethylpropanoate (D98) (803 mg, 3.84 mmol) and Cs2CO3 (1.36 g, 4.19 mmol) in dry DMF (3 ml) was heated to 80° C. overnight and then for a further 7 hours. The reaction mixture was then partitioned between EtOAc and H2O. The two layers were separated and the organic phase was washed with more H2O, brine, dried and concentrated a yellow oil. Purification of the residue by flash chromatography on silica gel [gradient ethyl acetate/cyclohexane] gave the title compound (356 mg, 37%) as a crystalline material. MS (ES) C15H17N3O2 requires 271, found 272 [M+H]+

Workup

  1. customThe reaction mixture was then partitioned between EtOAc and H2O
  2. customThe two layers were separated
  3. washthe organic phase was washed with more H2O, brine
  4. customdried
  5. concentrationconcentrated a yellow oil
  6. customPurification of the residue by flash chromatography on silica gel [gradient ethyl acetate/cyclohexane]

Sources & evidence

ORD record
ord-be2a687499be4d2da3725b5b83b2293f
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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