Cesium carbonate → Ethyl 3-(4-cyano-1H-indazol-1-yl)propanoate

HRID 2189790Notes

Reaction equation

HRID 2189790 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][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[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][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])#[N:11]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 68320Ethyl 3-bromopropionateHCID 247293471H-Indazole-4-carbonitrile

Product 1

HCID 59316734Ethyl 3-(4-cyano-1H-indazol-1-yl)propanoateYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1H-indazole-4-carbonitrile (0.716 g, 5 mmol), ethyl 3-bromopropanoate (1.276 ml, 10.00 mmol) and caesium carbonate (4.90 g, 15.00 mmol) were added to N,N-dimethylformamide (DMF) (20 ml) and the mixture was was heated to 90° C. for 80 minutes. The mixture was cooled before being extracted in a mixture of ethyl acetate and water. The organic fraction was washed with 3×30 ml portions of water, dried (MgSO4), filtered and evaporated. The crude product mixture was added to a Biotage column and was eluted with ethyl acetate/petrol 1:3 to give 0.95 g of the title compound. δH (CDCl3, 400 MHz) 1.17 (3H, t), 3.01 (2H, t), 4.08 (2H, q), 4.71 (2H, t), 7.46 (1H, dd), 7.54 (1H, dd), 7.81 (1H, d), 8.21 (1H, d).

Workup

  1. temperatureThe mixture was cooled
  2. extractionbefore being extracted in a mixture of ethyl acetate and water
  3. washThe organic fraction was washed with 3×30 ml portions of water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. additionThe crude product mixture was added to a Biotage column
  8. washwas eluted with ethyl acetate/petrol 1:3

Sources & evidence

ORD record
ord-d4e7cdb430384005883a18b109803075
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

Loading…