Dimethylformamide → (2-Butylpyrazolo(1,5-a)pyridin-3-yl)carbonyl benzonitrile

HRID 37205Notes

Reaction equation

HRID 37205 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[C:11]([CH2:19][CH2:20][CH2:21][CH3:22])=[N:12][N:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=23)=[O:9])=[CH:4][CH:3]=1.[CH3:23][N:24](C)C=O>O>[CH2:19]([C:11]1[C:10]([C:8]([C:5]2[CH:6]=[CH:7][CH:2]=[CH:3][C:4]=2[C:23]#[N:24])=[O:9])=[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][N:13]2[N:12]=1)[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 21472334(4-Bromophenyl)(2-butylpyrazolo(1,5-a)pyridin-3-yl) methanone

Product 1

HCID 86748690(2-Butylpyrazolo(1,5-a)pyridin-3-yl)carbonyl benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.5 g of the product of Example 1, 100 ml of dimethylformamide and 3 g of cuprous cyanide was refluxed for 24 hours and the reaction mixture was taken up in 400 ml of water and 400 ml of ethyl acetate, filtered and extracted with ethyl acetate. After drying and filtering, the solvents were eliminated under reduced pressure at a temperature of about 60° C. to obtain after chromatography on silica (essence G: 80/ethyl acetate: 20) 1.03 g of the expected product melting at 116° C.

Workup

  1. temperaturewas refluxed for 24 hours
  2. filtration400 ml of ethyl acetate, filtered
  3. extractionextracted with ethyl acetate
  4. customAfter drying
  5. filtrationfiltering
  6. customwere eliminated under reduced pressure at a temperature of about 60° C.

Sources & evidence

ORD record
ord-20e4c1800cc544f48aba3caf50071023
Source dataset
uspto-grants-1995_05
Patent number
US05420138

Reaction notes

Loading…