Water → 4-[1-(Phenylsulfonyl)-1H-indazol-3-yl]-1-piperazinecarbonitrile

HRID 609896Notes

Reaction equation

HRID 609896 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[N:9]=2)[CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].[N:32]#CBr.O>CS(C)=O>[C:20]1([S:17]([N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]([N:5]3[CH2:4][CH2:3][N:2]([C:1]#[N:32])[CH2:7][CH2:6]3)=[N:9]2)(=[O:18])=[O:19])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 148234251-(Benzenesulfonyl)-3-(4-methylpiperazin-1-yl)-1H-indazole

Product 1

HCID 148234434-[1-(Phenylsulfonyl)-1H-indazol-3-yl]-1-piperazinecarbonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred mixture of 3-(4-methyl-1-piperazinyl)-1-phenylsulfonyl-1H-indazole (237 g, 0.67 mole), K2CO3 (102 g, 0.74 mole) and dimethylsulfoxide (DMSO, 2000 ml), under nitrogen, was added cyanogen bromide (72 g, 0.68 mmol) dissolved in DMSO (525 ml). The reaction was stirred at ambient temperature for 5.5 hours and was then poured into H2O (71). The solid, which precipitated from solution, was collected by filtration and was washed well with H2O affording 168 g (68%) of product. A 5.2 g sample was recrystallized twice from ethanol-H2O yielding 4.0 g of 4-[1-(phenylsulfonyl)-1H-indazol-3-yl)]-1-piperazinecarbonitrile, m.p.=178-180° C.

Workup

  1. customThe solid, which precipitated from solution
  2. filtrationwas collected by filtration
  3. washwas washed well with H2O affording 168 g (68%) of product
  4. customA 5.2 g sample was recrystallized twice from ethanol-H2O yielding 4.0 g of 4-[1-(phenylsulfonyl)-1H-indazol-3-yl)]-1-piperazinecarbonitrile, m.p.=178-180° C.

Sources & evidence

ORD record
ord-04658bad874242e595b1a92f0553f029
Source dataset
uspto-grants-1999_12
Patent number
US05998417

Reaction notes

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