Water → 5-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrazolo[3,4-b]pyridine

HRID 520593Notes

Reaction equation

HRID 520593 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[S:13](Cl)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[N:9][N:8]([S:13]([C:16]3[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 404274545-Bromopyrazolo[3,4-b]pyridine

Product 1

HCID 666958975-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrazolo[3,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5-Bromo-1H-pyrazolo[3,4-b]pyridine (1.39 g) in DMF (6 ml) was cooled in an ice-bath under nitrogen and treated portionwise with sodium hydride (0.308 g) (60% dispersion in oil) over a period of about 15 min. The reaction was left to stir in the ice-bath for 40 min, then treated with tosyl chloride (1.469 g) in DMF (2 ml). The reaction was left to stir in the ice-bath under nitrogen and the ice left to melt overnight. The reaction was stirred for a total of 20 h. The reaction was treated cautiously with water (6 ml) and stirred for 5 min. The reaction was poured onto water (60 ml), filtered and the residue treated with DCM (20 ml). The mixture was stirred, and then pushed through a frit into a cartridge with a hydrophobic frit. The solution was allowed to drip through, and then this procedure was repeated with further DCM (2×15 ml). The combined filtrates were evaporated to dryness to give the title compound as a brown solid, 1.802 g.

Workup

  1. waitThe reaction was left
  2. waitThe reaction was left
  3. stirringstirred for 5 min
  4. additionThe reaction was poured onto water (60 ml)
  5. filtrationfiltered
  6. additionthe residue treated with DCM (20 ml)
  7. stirringThe mixture was stirred
  8. customThe combined filtrates were evaporated to dryness

Sources & evidence

ORD record
ord-fe6727c1882a41e6b56c63c842d1298c
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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