Water → 6-bromo-1-(4-methylbenzenesulfonyl)-1H-indazole-4-carbonitrile

HRID 38809Notes

Reaction equation

HRID 38809 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([C:13]#[N:14])[C:7]2[CH:8]=[N:9][NH:10][C:11]=2[CH:12]=1.[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.O>CN(C)C=O>[Br:3][C:4]1[CH:5]=[C:6]([C:13]#[N:14])[C:7]2[CH:8]=[N:9][N:10]([S:21]([C:18]3[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=3)(=[O:23])=[O:22])[C:11]=2[CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 247289186-Bromo-1H-indazole-4-carbonitrile

Product 1

HCID 666914596-bromo-1-(4-methylbenzenesulfonyl)-1H-indazole-4-carbonitrileYield 93.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.108 g, 4.50 mmol) was added to a stirred solution of 6-bromo-1H-indazole-4-carbonitrile (0.5 g, 2.252 mmol) in N,N-dimethylformamide (10 ml) at room temperature. The mixture was stirred at room temperature for 10 mins when p-toluenesulphonyl chloride (0.558 g, 2.93 mmol) was then added. The pale yellow suspension was stirred for 20 mins at room temperature. The mixture was poured into stirring water (100 ml) and the precipitated product collected by filtration. The cream coloured solid was dried in vacuo at 65° C. to give the title compound (0.794 g).

Workup

  1. additionwas then added
  2. additionThe mixture was poured
  3. filtrationthe precipitated product collected by filtration
  4. customwas dried in vacuo at 65° C.

Sources & evidence

ORD record
ord-14645866915c4a35a83a023edab8b8e1
Source dataset
uspto-grants-2013_09
Patent number
US08524751B2

Reaction notes

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