Acetic Acid → HCID 18998521, compound

HRID 2260570Notes

Reaction equation

HRID 2260570 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([N:12]1[C:16]2=[N:17][CH:18]=[CH:19][C:20](Cl)=[C:15]2[CH:14]=[N:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O)(=O)C>CN(C)C=O>[N:1]([C:20]1[CH:19]=[CH:18][N:17]=[C:16]2[N:12]([CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:13]=[CH:14][C:15]=12)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 33557Sodium AzideHCID 18998588HCID 18998588, compound

Product 1

HCID 18998521HCID 18998521, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (2.5 g) was added to a solution (50 ml) of 1-benzyl-4-chloro-1H-pyrazolo[3,4-b]pyridine (4.7 g) in dimethylformamide and the mixture was stirred at 100°-120° C. for 1 hour. After completion of the reaction, the reaction mixture was poured into ice water, made acidic with acetic acid and extracted with ethyl acetate. The extract was washed with water, dried and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography to give 2.7 g of 4-azido-1-benzyl-1H-pyrazolo[3,4-b]pyridine.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2b83d7e462b74ca8a3dac5635b9d9dbd
Source dataset
uspto-grants-1995_12
Patent number
US05478838

Reaction notes

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