N-bromobutanimide → CID 14590535

HRID 490891Notes

Reaction equation

HRID 490891 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][N:7]=[C:6]2[N:15](CC)[N:16]=[CH:17][C:5]=12)[CH3:2].BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]1[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][N:7]=[C:6]2[NH:15][N:16]=[CH:17][C:5]=12)[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 13072976Ethyl 4-ethoxy-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

Product 1

HCID 14590535CID 14590535Yield 50.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of Intermediate 35 (1.0 g, 3.8 mmol) and N-bromosuccinimide (1.49 g, 8.4 mmol) in carbon tetrachloride (35 ml) was heated at reflux for 3 hours. The reaction mixture was cooled in an ice-bath and the precipitate filtered. The filtrate was concentrated in vacuo and the residue dissolved in tetrahydrofuran (12.5 ml). Water (3.5 ml) and saturated sodium carbonate solution (3 ml) were added and the mixture stirred at 20° C. for 18 hours. The reaction was diluted with water and extracted with ethyl acetate. The combined organic phases were dried Na2SO4) and evaporated in vacuo. The residue was purified on an SPE cartridge (silica, 20 g) eluting with dichloromethane, chloroform, then chloroform:methanol (99:1, 49:1, 19:1 then 9:1). Appropriate fractions were combined and evaporated in vacuo to afford Intermediate 36 as an off-white solid (0.45 g). LCMS showed MH++236, TRET=2.46 min.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe reaction mixture was cooled in an ice-bath
  4. filtrationthe precipitate filtered
  5. concentrationThe filtrate was concentrated in vacuo
  6. dissolutionthe residue dissolved in tetrahydrofuran (12.5 ml)
  7. additionWater (3.5 ml) and saturated sodium carbonate solution (3 ml) were added
  8. additionThe reaction was diluted with water
  9. extractionextracted with ethyl acetate
  10. customevaporated in vacuo
  11. customThe residue was purified on an SPE cartridge (silica, 20 g)
  12. washeluting with dichloromethane, chloroform
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-0bfa5079a52f4029a6e3aa97174d01d0
Source dataset
uspto-grants-2009_05
Patent number
US07528148B2

Reaction notes

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