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

HRID 520502Notes

Reaction equation

HRID 520502 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-2a98d72c7f9c41578801c257c6b63034
Source dataset
uspto-grants-2016_05
Patent number
US09326987B2

Reaction notes

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