Benzenesulfonyl chloride → HCID 58356416, compound

HRID 244710Notes

Reaction equation

HRID 244710 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[CH:12]=[N:11][NH:10][C:7]2=[N:8][CH:9]=1.[H][H].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O.O>[Br:3][C:4]1[CH:5]=[C:6]2[CH:12]=[N:11][N:10]([S:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:23])=[O:22])[C:7]2=[N:8][CH:9]=1

Participants

7

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 404274545-Bromopyrazolo[3,4-b]pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 58356416HCID 58356416, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium Hydride (0.667 g, 16.66 mmol) was added portion-wise over 15 mins to a stirred solution of 5-bromo-1H-pyrazolo[3,4-b]pyridine (3 g, 15.15 mmol, available from ChemGenx LLC) in N,N-dimethylformamide (30 ml) that had been cooled in an ice bath to 0° C. and placed under nitrogen. The mixture was stirred for 20 mins, until hydrogen evolution ceased, and then benzenesulfonyl chloride (2.148 ml, 16.66 mmol) was added. The mixture was stirred for 18 hours, letting the ice melt over this time. The solution was poured into stirring water (10 ml) and rapidly stirred for 15 mins. The mixture was then poured onto water (70 ml) and filtered. The orange solid obtained was dried in the vacuum oven for 18 h to afford the title compound (3.86 g).

Workup

  1. additionThe solution was poured
  2. stirringrapidly stirred for 15 mins
  3. additionThe mixture was then poured onto water (70 ml)
  4. filtrationfiltered
  5. customThe orange solid obtained
  6. customwas dried in the vacuum oven for 18 h

Sources & evidence

ORD record
ord-5d51491f46b942b49f91ef140394fd29
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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